And so it goes with fashion, when I wrote the Creative Pragmatist it was founded on style principles that aren’t abstract - unless they are, to you. What I mean is, you’ll either connect viscerally with their meaning and purpose and it will stick with you forever. And more often, will seep in to other areas of your life. Or you’ll think it’s bullshit - and fyi, many of my friends do. It’s an “IYKYK” sort of thing, it’s transformative for someone who has an ease about them (or desires one!), is deeply interested about what is new and next and why, and respects the knowledge that only time and the study of it can bring. We’re not all like that, one is not better than another, just different. But if you are, then these stye principles, not rules, will hit deep.

Below are excerpts from The Creative Pragmatist where I lay out the principle of Irony. Literally in a way designed to give you the tools to think of why it’s employed and understand that one persons ironic may be another’s average.

So you can see, I have a lot of friends right now who are scratching their head and thinking how much they love the “not this.” And they’d be right to do so- because objectively it looks lovely. But I know how I would feel in it, because it is hardly chill, lacks visual curiosity (to me), and it is classic. One of three. I need all three for balance.

I wrote The Creative Pragmatist for people who seek an intellectual conversation around personal style - not the banter of it all. That banter weighed so heavily on me for years, the conversations around a fashion show, coffee with a press person, I’d break out in literal and figurative hives. It turns out, many others felt the same way, we just couldn’t tell who the people were that didn’t want to end with a quippy statement about bracelets as candy for your arms.

If you give a Mouse a Cookie….

I wrote Almost Reckless because people began making the connection that these “style principles” were really fundamentally much deeper than pairing red with pink. They made sense as a way to live your life as well, a better life. It’s a good read.

If you’ve read the books, I’d love your thoughts here - what principles really hit, which ones moved well beyond the closet to your everyday life. OK?

In my book The Creative Pragmatist: An Intelligent Conversation About Personal Style I illustrate the scale to better drive the point home:

Sarah leans highly creative, you should see her some days in the office - chic but definitely registering a bit lower on pragmatism, I’ve no idea how she navigated the subway sometimes but that’s her feistiness full and present. Traci’s always strolling in like a cucumber, very cool in her eased out put tailored looks that have a twist that dares anyone to be foolish enough to define her in one word. And me, most days I’m skating right in the middle, veering to the left and the right as the day, place or time demands.

The CP Scale becomes most present in our bi-annual Fundamentals collection. Because they are the core ingredients one uses to make great things that reflect their personality. If we were cooking, these would be akin to Olive oil, sugar and salt. On this episode, Sarah, Traci and myself style Sacha our model - so you can see the lens through which we interpret pieces that serve as a basic but refused to be defined as such.

We each had 5 pieces to work with: a tropical wool skirt, pale pink denim, our lantern skirt, the twill trouser, and camouflage. There’s a clear thruline between us all - each look Traci and Sarah put together I hadn’t considered, but absolutely would. I was inspired because it was a convo between people who “get” each other.

The Tropical Wool Skirt

Sarah paired it with the Black Nylon Liam and the Perfect tee in layers. I added my favorite ribbed knit that’s on sale from spring, and wanted the accent of the cardigan in that good ring 3. Traci killed her look with the resort belted tank on sale, so bonus.

The Pink Denim

Sarah paired it with the sheer silk voile top on sale from spring and clean black flip flops. I put it with a bodysuit we did from 2022, and my NEW FAVE Jacket here in the most goodest ever ring 3 color and my brick red toe ring sandals. Traci styled heres with charcoal grey and the pink toe ring with worked SO chic!

The Lantern Skirt

Sarah paired hers with the red twill shirt; I styled mine as I’m packing for summer with the brown tube top and an easy sweater at my waist and olive slides; traci topped hers with the voile top on sale and our favorite sandal.

And then the red pant in the trouser and in the pleated. Sarah put hers with the simple cashmere hoodie and the brick version of best sandal ever. I am headed out west here so wanted it with denim and traci layered it up in a neutral top and tank - both of which are on sale so yay for you.

Let me know in the comments who you think won the challenge. I’m deeply curious.

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New episodes every Monday. Part of the Almost Reckless universe from CP Media.

Thursday morning, rush hour, the A train headed to Manhattan. I’m just going to be super transparent here—there was a man who had gotten on the train standing next to me who happened to be, by any standard, really handsome. On any normal day, I would glance up every now and then, text my friends that I have a new subway crush, and then disappear into the swarm of New Yorkers headed to their destinations. However, this wasn’t a normal day. I found myself fully engaging in a self-inflicted internal argument. There was something in me that felt curious…curious enough to do something about it. So, like any reasonable adult, I brokered a deal with myself. The deal was this: if there is a pen in my bag, I’ll give him my number on a piece of paper. If not, it’ll be chalked up to a missed connection. Was there a small part of me hoping that there wouldn’t be a pen in my bag? Absolutely. Was there a pen in my bag? Absolutely. I never have a pen on me.

I am, after all, a woman of principle. I held myself to my ultimatum. There I was, tearing off a piece of a Whole Foods receipt, clumsily jotting down “Stella” and my phone number.

Mind you, I have two stops left until my destination—so I’m stuck holding this piece of paper. Awesome. After what felt like ages, the A train roars out of the tunnel and pulls up to the platform. Before I could even talk myself out of this interaction, my hand was already outstretched, handing the piece of paper to the man. “Wait, this is for you,” I say. I hadn’t thought about the speaking part (ha, ha).

He smiled (confused), I smiled (also confused). The doors shut, the train barreled to its next stop.

I did indeed disappear into the swarm of New Yorkers headed to their destinations—but this time, with a sense of gratification that gave me pause. As I was replaying the interaction in my mind (probably twenty times), the excitement didn’t come from the prospect of hearing from this man (albeit, a fun byproduct). It came from something else entirely. Feeling, being, an active participant in my own day—in my brain. Embracing discomfort on my own volition.

Embracing friction, even if it’s within myself.

Why did something that could be deemed a humiliation ritual put me in such an optimistic mood? After letting this question marinate for a minute, it hit me. I experienced something that wasn’t served up to me on a silver platter by The Algorithm. There was nothing contributing to that interaction that had anything to do with the tech wizards that eat our data for breakfast. It ultimately came down to existing at the same time and same place as this individual, and seizing the moment.

I don’t like to make sweeping generalizations, but for the sake of this story, I will—so bear with me. Gen Z is (generally speaking, okay) a self-declared socially anxious generation. And I would argue that it has crippled our ability to create moments of connectivity amongst ourselves. I don’t know that I fully understood the degree to which Gen Z has consented to outsourcing our thinking until I experienced this moment. And I would reason that, as a result of this outsourced thinking, our DOING has been squashed. For lack of a better word.

Later that day, I wound up dissecting the concept of “getting to the grey” with Amy. And if you’ve listened to the podcast that I co-host, The Grey Area, you’ll understand that not everything is black and white—grey is a color, too. It’s the proverbial middle-ground that grants us permission to change our minds, exercise critical thinking, and experience a range of discomfort that makes the human experience richer. Good old-fashioned nuance. They don’t make it like they used to—but this doesn’t have to be the case. It does, however, require getting uncomfortable on purpose, which you might instinctively and viscerally reject. I understand this—we all love to be cozy. But we might be so cozy that we are beginning to err on the extreme end of cabin fever. And amazing things can happen when you get outside.

I typically don’t wrap these articles with a call to action, but I would like to now. If you’ve listened are a fellow Gen Zer, or if you know a fellow Gen Zer, I would urge you to do something this week that extracts you from The Algorithm. Smile at someone on the train. Tell someone you like their shoes (granted you actually like their shoes). Ask someone a question. Shoot your shot! I would wager that you might end up having an interesting conversation that you may not have otherwise had. Maybe you will be shrugged off, maybe you will learn something new. But one thing is for certain: you will walk away from the experience with the knowledge that you did something that made you feel like you have a pulse.

If you haven’t already, I would highly encourage you to pick up a copy of Amy’s book, Almost Reckless: A Creative and Pragmatic Approach to Taking Risks. It’s an incredible guide for codifying your principles to help you extract yourself from the algorithm when the moment calls for it. I’ve read it myself, and it is genuinely a one-of-a-kind guide to sharpening your internal measuring stick for taking risks.

Houseman was built for regulars. This is not an interpretation; it is close to a mission statement. The name comes from husmanskost - a Scandinavian word meaning, roughly, “everyday food” - and when chef Ned Baldwin opened the restaurant in June of 2015, the question he kept asking himself was disarmingly simple: what’s in the restaurant that I want to go to? The answer sits on a quiet, tree-lined stretch of Greenwich Street in Hudson Square, a sliver of lower Manhattan that is technically west of SoHo, south of the West Village, and north of Tribeca, and that nobody - including, charmingly, the restaurant itself - can quite claim belongs to any of them.

Baldwin’s path to that question is its own story. He earned an MA in sculpture from Yale and spent years as a visual artist and builder before deciding, at 36, that the thing quietly consuming his attention - cooking - deserved his full commitment. He apprenticed under Alain Ducasse and Jean-Georges Vongerichten, passed through Tom Colicchio’s Craft, and eventually became chef de cuisine at Prune, Gabrielle Hamilton’s East Village institution, where he spent the better part of five years absorbing a philosophy that prized honesty over spectacle. All of which is to say: Houseman is what happens when a man who spent half his life learning how to build things decides to build a restaurant - not a concept, not a brand, but the actual thing, with old walls left old, schoolhouse chairs, a zinc bar, and tables cut from reclaimed bowling alley maple.

We went on a Friday night and sat at the bar, which is where Houseman makes its clearest case. The room runs long and narrow - whitewashed brick on one side, raw weathered plaster on the other, branching fixtures overhead casting the kind of light that flatters everyone equally - and from a stool at the zinc you can watch the whole operation breathe. What struck me first was not the food. It was the greetings. Diners walking in and being received by name. The unhurried conversation between the staff and a man eating alone who had clearly done this exact thing, in this exact seat, many times before. Our bartender was the kind you remember - knowledgeable without performing it, attentive without hovering, the sort of person who makes a seat at the bar feel less like a consolation prize and more like the room’s best-kept secret. We drank Mexican Cokes from the bottle, cold and sweet with real sugar, and at no point did anyone make us feel that this was anything less than a complete and correct order.

The food began with the Smoked Bluefish and the Fava Hummus. The bluefish - smoked in-house, folded into something cool and creamy, capped with fresh dill - came with seeded crackers built for structural duty, and the whole thing tasted like a fisherman’s idea of luxury, which, given that Baldwin is a devoted fisherman whose menu always carries whatever is running locally, is exactly what it was. The hummus wore a pool of marinated olives at its center and a dusting of za’atar at its edges, with thick slabs of grilled sourdough whose char carried into everything it touched. Two openers, two different instincts - one from the water, one from the pantry - both landing in the same unhurried register.

The Butter Lettuce, Snap Peas, Lemon, Labne was the surprise of the night. A pile of impossibly fresh butter lettuce - crisp, cold, structurally perfect - dressed in labne flecked with poppy seeds, painted with threads of lemon zest and whole mint leaves, the citrus lifting everything without announcing itself. A salad this simple has nowhere to hide, and so it stands entirely in the open - every leaf accountable, every element doing precisely what it claims to do, holding your attention with nothing but freshness and proportion. It was, genuinely, one of the best things we ate.

The Houseman Burger came the way burgers should - unfussy, properly cooked, a cool, barely-pickled cucumber standing upright in its own ceramic cup like it had somewhere to be. If the steak is the plate this city makes pilgrimages for, the burger is the one the neighborhood orders without opening the menu - the Tuesday answer, the plainest and most fluent expression of husmanskost in the building. There is a particular comfort in a burger that knows exactly what it is.

The Steak and Fries is the headline, and it earns the type size. New York Magazine has called Houseman’s hanger steak the best in the city, and the plate that reached us made the case without apparent effort - thick slices cooked to a deep, even rose, the crust dark and mineral, confit garlic cloves and a sprig of thyme resting on top, a ramekin of aioli alongside. And the fries. I have eaten a great many French fry in my life with ample enthusiasm, and these are my favorite kind, full stop - thin but not shoestring, golden to the point of amber, crisp through the entire bite, and carrying, just beneath the salt, a faint bright note of vinegar - the ghost of a salt-and-vinegar chip, the kind of detail you notice mid-sentence and lose the sentence over. The Michelin Guide describes them as fluffy, crispy, and perfectly salted, which is accurate and still somehow undersells the experience of eating them at the bar on a Friday night with a cold Mexican Coke.

There is a small illustration on the Houseman menu - two cheerful, vaguely mythological creatures strolling through grass - captioned with four words: A Day like any other. I keep thinking about that caption, because it is the entire restaurant in a sentence. Houseman will hold your birthday, your anniversary, your celebration, and hold them well - but its quiet genius is the Thursday. The steak and a glass of red, alone at the bar, no reservation, no performance of any kind - just a room that knows you, food made by people who mean it, and the quiet, durable pleasure of being a regular somewhere. From my days on the line I can tell you that those people are the ones who keep a restaurant alive. Houseman seems to have understood this from the very beginning, and built itself, plank by reclaimed plank, in their image.

Dinner nightly. Lunch weekdays, brunch on weekends. Walk in, sit at the bar.

I have been wondering lately whether understanding is something that can be accessed in the middle of an experience, or whether it is, by its nature, something that only becomes available after. Whether the clarity that arrives at the end is a reward for finishing, or simply a function of distance - a perspective that is physically impossible to reach from inside the terrain.

Maps. Could maps provide an answer?

The great maps of the world - the ones that revealed coastlines, that traced river systems across continents, that gave shape to mountain ranges no one had yet seen from above - were not drawn in real time. They could not be. The explorer’s job was to walk the terrain, to feel the river’s current, to register the grade of the mountain in the legs, to notice when the path narrowed without warning and to push through it anyway. The experience was bodily, immediate, ground-level - and from the ground, the territory has no shape. It is trees and weather and the next hill and the mud you are standing in right now. You cannot see the coastline when you are on it. You can only walk it.

The map came after. Often drawn by the same person who walked the land, but working in a different mode - no longer moving, no longer reacting, no longer in the weather. Sitting still, translating the body’s memory into lines on paper. And in that translation, something remarkable would happen: what had been suffered as chaos on the ground would emerge, from above, as design. The river bent because of the geology beneath it. The path narrowed because it was passing through a ridge that, from above, you could see had no alternative route. The stretch that felt impossibly difficult - the one where you questioned why you were out here at all - sat directly above a fault line, a place where the earth itself was under pressure. You could not have known that from the ground. The map does not just record where you went. It explains why the going felt the way it did.

I think about this when I think about the last several months of my life - training for something that I took far more seriously than it probably warranted, putting my body and my mind and, if I am being honest, the people closest to me through a kind of stress that, in retrospect, was disproportionate to the event itself. While I was in it, I could not see that. The terrain was just hard, and I assumed the hardness was the point, and I put my head down and walked. It was only after - standing on the other side, no longer in the weather - that I could look back and see the shape of what I had actually been moving through. The stress was real, but the map it left behind is more interesting than the suffering suggested. The thing I thought I was training for and the thing I was actually learning turned out to be two different places on the same map, and I could not have drawn the line between them while I was still walking.

There are people in my life who have come and gone - some by choice, some not - and from inside those experiences, each one felt like its own isolated territory. A friendship that arrived late but deep, that skipped the slow accumulation of years and went straight to something essential, the kind where you never said goodbye because it was always see you soon. A scene that once felt like yours, that you moved through with the certainty of someone who belonged, until one day the territory looked different, and you could not tell whether the landscape had shifted or whether you had simply walked far enough to see it from a new angle. From the ground, these feel like separate places. Unrelated stretches of terrain with nothing connecting them. But I am starting to suspect - and I can only suspect, because I have not yet walked far enough to draw the full map - that they are contours on the same landscape, and that the connections between them will only become legible from a distance I have not yet reached.

This is, I think, the hardest part of being in your twenties, or perhaps of being alive at any point along the walk: the desire for the map while you are still in the terrain. The wanting to see the shape of your life while you are still inside it, to understand the logic of the path before the path has finished revealing itself. And the frustration - sometimes grief, sometimes restlessness, sometimes just a low hum of confusion - of knowing that the clarity you want is real, that it exists, but that it is not available from where you are standing. It requires more walking. It requires finishing the stretch you are on, and then sitting still long enough to translate it.

I do not think you can draw a map of a place you have not yet left. I think the desire to do so is natural and human and probably universal, but I also think the willingness to keep walking without one - to trust that the shape will emerge once you have covered enough ground to see it - is not naivety. It is the condition of the work. The explorer does not get the map and then walk the terrain. The explorer walks the terrain and then gets the map. And the map, when it finally comes, does not just show where you have been. It shows you why you went. And sometimes - not always, but sometimes - it shows you where you were heading all along, even when you were certain you were lost.

New episodes every Monday. Part of the Almost Reckless universe from CP Media.

IF YOU…..

Are frustrated because your closet has no grounding - either

• Because life hasn’t given you the time yet to build your wardrobe. It’s nothing you’ll do in one swoop, you’re committed to buying thoughtfully - no cheap stuff, no fast fashion. These are investments for you and they need to deliver.

• You’ve invested over time in a wardrobe that seems bursting at the seams with oddly nothing to ground the pieces you’ve accumulated. You feel you’ve nothing to wear when the sheer quantity in your closet suggests differently.

1. The tropical wool Scotty pant. With the matching blazer it says “I take myself seriously”. It’s can chill out with a sandal and be made into a jogger with a scrunchie hack at the ankle. The navy here is SUPER dark and rich. Black is good too Always. It’s year round and meant for forever. And if you’ve got a range of tops, designed out, big in nature - the ultimate balancing act here.

2. The blazer. The material is robust with a twill like texture to it - that means if you pair it with any black tropical wool pant, it will give a suitlike effect with an interesting mix of textures - that’s key, enough differentiation that the mix has intent. This jkt elevates the hell out of casual blue denim, with black denim it’s ready for a super event, with white track pants your just cool AF.

3. This crochet top may surprise you as such a fundamentally perfect investment or item that gives glue to chaos. But these tops that are highly simplistic (but not) in design, and manage to give texture without highjacking the story line, are pieces you will pull out and wear over and over. Shocking, until it isn’t.

IF YOU…..

Need pieces with some ‘tude that EXEMPLIFY CMC in one item, these are your bets.

1. The ribbed stretch knit here epitomizes my frustration with technology. We can put a man on the moon, but I can’t find a way for you to touch the richness of this knit. This filled my gap for a slim tee like item that was ultra luxe - enough to go to the fanciest dinner, the most uptight business meeting, yet also wear with ribbed jeans and sandals on the weekend.

2. The trouser skirt delivers so much style but plays nice just out for lunch with flip flops and a tee. It fits like all our trouser skirts - lower on the waist - check your hip measurements here on this one for fit. I wear the size 4- I have 27” waist and 38” hips. I can not wear a 2- this lays on the body - neither fitted nor loose.

3. The racerback tank. My tees have to have a point of view. You see, tee material is already CHILL and CLASSIC by nature - if the neckline is “meh” then you miss the MODERN. This one is CMC all the way and why it’s my dinner tee, my tee under a sheer top tee, my tee under a blazer when I want a bare look tee.

IF YOU…….

These are the SPONTAINERS - they are items in your closet that are perfect for when an event suddenly comes up and you absolutely don’t have time or desire to wig out on what to wear. All three of these items fit a range of events….

1. This is the dress that morphs with a shoe. A brogue makes it Paris Fashion week “I’ve got walking to do and look accidentally chic”; a flat sandal makes it dinner in the South of France; a sharp pointy toe slingback is dressy dinner in NYC, a bright pink sandal is perfect for that wedding where everyone’s wearing fluffy prints and you just simply can’t go there.

2. The skirt that took me just last week to “brunch” on the upper east side of NYC where I wasn’t sure what people would wear and needed to be refined but very much myself. With a sleek black tank it’s dinner in Milan. With tall boots and a grey sweater it’s October in Vienna.

3. The denim printed short here - are you in marketing and have a business pitch? I’d buy what ever creative you’re selling me. Dinner with friends in San Fran? With flat sandals for lunch in Florence? With big black sweater tall boots in Nov? Done.

IF YOU…..

Are like a cat waiting to pounce on the “IT” item that you have been wanting to pull the trigger on…..

1. You can not FULLY appreciate this jacket until you try it on. The rich material that is rude to call sweatshirting; the fleece, the sculpted shape. This is not athleisure wear, this is what you wear with a skirt in Paris to give serious chill Modernity.

2. The soft drapey leather moto jacket. I’ll say no more.

3. The Liam blazer in the wool angora. Double faced and super rich. It’s a suit, it’s an outerwear piece, it’s the coziest refined piece for an airplane.

IF YOU…….

Know the value of a “VALVE” item - they either turn up an item and give It punch, or they take it down a notch. Here are two to consider:

1. The shoulder hinged tee. This is a ponte-like weight material - that means it has serious guts. This elevates a pair of denim into “I’m going somewhere very chic” mode; yet paired with a big black wideleg chic trouser it says “all this chicness is accidental, I don’t take myself that seriously.”

2. The reverse sleeve top - I always look for high impact that requires someone to give a second look to register. It adds so much modernity to a slouchy pair of denim, but it plays exactly right with a highly sculpted pair of pants that needs an equal pairing but not a direct competitor.

IF YOU…..

Need pieces that can go to extremes - with a shift of attitude and locale.

1. The white dress here - I may go to a beach dinner in this, but I could see a friend getting married in it. It’s that substantial.

2. The chassis hoop skirt - it’s modern casual for day - and at the same time this hit numerous red carpets for movie premiers where individuals dialed it up but still were able to play it cool.

3. The skirt that manages to be so effortless for a stroll, yet….can do this below:

   

   IF YOU…..

   Need some serious glue in your closet to bring everything together. The “RING 3” tops are your everything.

1. The Luxe ribbed tank. You may have noticed we are very judicious with that word. When we use it means it is indeed a super rich fabrication that is robust and refined simultaneously. Wear this with any of the bright colors in your closet for a calming effect; or pair with your neutrals to expand your range and outfitting options.

2. The tank with all the sexiness implied with this neckline and all the pragmatism that a ring 3 delivers is holy-grail-ish.

3. The bodysuit - I live in them - pair this with black pants and a white jacket - you give depth to ring 2 neutrals; wear it with a hot pink slip skirt and you’ve totally given that guy some much needed chill. Can you see it????

NOTE: Keturah hosted a STYLE CLASS SALE marathon on Friday - reviewing fits, questions, all the good deets. You can FIND IT HERE.

For five years between 1975 and 1980, John Lennon mostly did not make music. He baked bread. He read. He stayed home in the Dakota with his son Sean, who had been born in October of ’75 - on Lennon’s own thirty-fifth birthday - and let the press and the industry and the myth of John Lennon carry on without him. By Lennon’s own account, and by those of the people closest to him, it was one of the happiest stretches of his adult life. Beautiful Boy (Darling Boy) is the song he wrote about it - a lullaby for a five-year-old, recorded for Double Fantasy and released in November of 1980, three weeks before Lennon was killed on the sidewalk outside the same building where he had spent those five years. It is the song that opens this month’s curation, and there is a long answer for why, but the short one is that it has been my favorite summer song for as long as I can remember.

Beautiful Boy has carried me through more than a few hard days, the kind where the floor tilts and you reach for the one thing you know will hold. I have never needed to understand why a lullaby written for a five-year-old is that thing. It is nostalgic without belonging to any particular memory. It is a song for a son, and for a father, and for a friend, and for anyone who has ever loved someone enough to be a little afraid of it. It moves the way a wave does in the seconds before it breaks - cautious, gathering, almost reluctant - and then folds over against a cliff-edged shore, all at once and gently at the same time. It is the feeling of salt and sand still in your hair hours after the water. It is the warm smell of wheat in a field and cherry trees in bloom drifting through a window you forgot you left open. It takes your past and your future and sets them down in the same place, and what is left over, the remainder of that equation, is presence. Just presence.

That, I think, is what Lennon found in those five years of bread and books and staying home - not a retreat from his life but the center of it. Every day in every way it’s getting better and better, he sings, and then, life is what happens to you while you’re busy making other plans. He had been the most famous man alive, and he traded the noise of it for an unrepeatable thing happening inside one apartment, between a father and his boy. The records and the press and the legend, it turned out, had only ever been the way of getting to that room. The boy was the part he did not want to miss. And that is the feeling of June to me - not the deep of summer, not the first thought of fall, just the open door of the season.

Switching grooves, there is a short film I have not been able to stop watching - The Shape of Paris, five minutes of the Canadian skateboarder Andy Anderson moving through the city, filmed by Brett Novak. I say skateboarding, but the word undersells what he does. Anderson skates in a style that reaches all the way back to the freestyle era of the sport and then somehow forward at the same time. The effect is less like tricks than like figure skating - if the rink were an entire city and the skater carried it under his feet wherever he went. He floats. He spins through a courtyard, carves a slow line around a fountain, turns a flight of museum steps into something graceful instead of reckless. Paris in the summer has rarely looked the way Novak frames it here. And running underneath all of it is the song I actually came here to tell you about - Gone Down the River, by Fletcher C Johnson - scoring the film so exactly that I had to go hunting for its name the moment it ended, a loose, loping folk thing that sounds like it was caught in a single take on somebody’s back porch, all warmth and no polish. The song is barely a story, more a wandering catalogue of strange and beautiful things a drifter has seen crossing the country coast to coast, none of it resolving, none of it building toward a chorus that would tidy it up and explain it.

The other track to slow down for is Mo Se B’ólá tán, by Dele Sosimi with The Estuary 21 and the British artist who records under the name Get Cape. Wear Cape. Fly. Sosimi is one of the great living Afrobeat musicians - he was the rhythm keyboardist in Fela Kuti’s Egypt 80 from 1979 to 1986, then co-founded Positive Force with Femi Kuti and was the band’s musical director until 1994. The pedigree matters because Afrobeat is one of those forms where lineage is not a credit on a sleeve, it is an inheritance - knowledge passed from one player to another in the room, on the bandstand, in person. Mo Se B’ólá tán moves the way Sosimi moves - patiently, in layers, with the conviction that the groove is not building toward anything. The groove is the point.

On our way out, two more worthy of honorable mention: Stay a While, the Sister Sledge edit by The Revenge, sits second on the playlist on purpose - it is the song that opens the door right after Beautiful Boy closes it, gently, behind you. And Touch, by Levitation Room, a psychedelic rock band out of Los Angeles and the next Tibi Close Friends project. I will save the proper introduction for when that piece arrives but take this as the first warm signal of what is coming. There is energy on this curation, plenty, but the note underneath everything is weightlessness, the feeling of having shed something. A coat. A heaviness you forgot you were carrying. The brace you keep in your shoulders all winter long. July and August are still out there, hotter and slower - but that is later. June is the door. Stand in it.

p.s. tracks sixteen, seventeen, and eighteen - Secret Life, The Lie, and Dirt - Sid Simons, recorded live at 666 Studios and out now on every platform, the first time Tibi Close Friends has lived on the DSPs.

Any company should want to hire this person. If businesses scouted the same way the NY Rangers do, they’d be fighting crawling over others to recruit her.

Yet at the same time, I’m pretty sure this story didn’t land on her resume. And I’m sure she didn’t distill the experience to:

“Leveraged hotel resources to tap in to a captive community with a needs based approach delivering excellence with a scalable proposition optimized for maximum ROI.”

Yet resumes continue on in their same state. Or worse now - thank you AI for handing us “resume slop.” I asked Chat: what’s a better way to say that “I am a creative pragmatic thinker” and it replied: “I have hypothesis-driven problem solving skill and actionable insights.” Sure, ok. But if I read this, how would I know you’d made bank in the Hilton’s elevator bank?

The point is, I don’t. But the bigger point is, you don’t either. This is what I mean.

Resumes can define us because they say a lot - and many of us think they say everything. This sequential timeline of our experiences neatly laid out in black in white. How do you know what you’re really good at, where you excel, if you value yourself on the merits of a “Trad Resume?” What we’ve achieved, or think we have the possibility of doing, is often framed in this limited and sometimes excessively convoluted vernacular and it doesn’t give us permission to think widely about what could be. In fact, not only does it not give permission, but it kind of taunts you - like “who are you to think you can do xyz????

I’m making a case here for creating your own Reckless Resume. I’m not suggesting you submit this to JP Morgan along with your interest in the derivative’s market. But I am suggesting that when you build one for yourself, you’ll have a far greater sense of the unique bundle of skills you bring to any job- even if, and ESPECIALLY IF, it’s just the job of living your life.

DO THIS

Build your Reckless Resume.

The left side, that’s the “Trad Resume”. We’re going to focus on the right side. Start brain dumping the simple, seemingly inconsequential things you can recall doing, growing up. The things that stuck with you, make you laugh, cringe or cry. If you’re extracting something you did 15 or 40 years (depending Gen Z or X here), the fact that it’s sitting there waiting to be plucked from obscurity tells you something. Now drill hard on them- what were you really exhibiting? If you treated them the way you would a resume entry, how would you sum them up?

For me, the left side of my resume allowed me to get a fashion brand off the ground (advertising, business, drawing skills), but the right side is what helped give the brand its longevity and competitive distinction. Headlines about AI domination, and you can see that the left side is where many of our skills have become commodified. It’s the right side that takes what we do and makes us human, makes us individuals, makes us unreplicable.

When you write your Reckless Resume, it forces you to think of the “so what” of your past actions and you start connecting dots - understanding viscerally why you’re really good at some things, and at others …. not so much. No one is a 10 out of 10 on everything - and that’s OK, as long one knows it. Sometimes our weaknesses are identified not to improve on them but for no other reason to know where we will need to augment. Knowledge is power and it’s why I would never hire my carbon copy. Traci, our head of design, is my perfect foil.

I’ll give you an example of an event that was so much more than the sum of its parts and lands squarely on my Reckless Resume.

I skipped out midway through an exam my freshman year in college to fake a kidney ailment because I found myself wholly unprepared and facing a failing grade. I chose the kidney because my dad suffered from stones and I knew the symptoms. I went immediately to the school Emergency Room as proof of my “whereabouts” and was told by the very handsome student doctor that the symptoms I’d identified were “consistent with an acute sexually transmitted venereal disease”. Whilst being tortured for the next couple of hours with my feet in stirrups I was playing out how I’d share this with my history teacher and then how this will be spun for laughs over drinks with my friends.

But if I translate what happened to resume speak, I would say I was able to:

• Quickly assess if a situation would result in a failed outcome, no matter how much more sweat equity is put in (I knew I was going to get an F, a D at best).

• Identify options and determine risk versus reward

• Execute a sharp pivot that required fast thinking with no time for information gathering

• Exhibit a determination to not accept failure as fate

• See the humor and find perspective

This isn’t about creating a delusional story line for yourself. It’s about uncovering those attributes that get hidden under the constraints of how society/schooling/family etc. frames success. It’s also about using what you have - because this is where you find a great equalizer. A combination of these experiences play a huge role in determining our success - but the thing is, if you allow them to stay buried and never articulate them, then it’s hard to actually put them in to play. Once you put words to something, you can get your arms around it, own it and take action. Ok?

My book Almost Reckless helps you put a vocabulary to what you have to offer. Because once you can say it, you can be it. And that’s a great thing. You can purchase here.

New episodes every Monday. Part of the Almost Reckless universe from CP Media.

What followed was one of the most grounding conversations I have heard in a long time. Not because it was full of groundbreaking revelations - Bobbi Brown is not in the business of shock value, and that itself is part of the point - but because almost everything she said cut directly against the noise that my generation has been marinating in since we were old enough to open Instagram. The highlight reels, the funding announcements, the carefully constructed personas designed to signal that you have arrived at a place most of us are still trying to find on the map.

Here is what stayed with me.

Bobbi Brown was told, at various points in her career, that she was not enough. Not glamorous enough, not edgy enough, not fabulous enough to be taken seriously in an industry that rewarded bad behavior and punished normalcy. A stylist once ridiculed her into buying leather pants she never wore. Someone suggested she wear a hat with a feather in it because, at her height, she needed something for people to notice when she walked into a room. She was told that no one wants beauty advice from a soccer mom. And through all of it - the pressure, the noise, the well-meaning people trying to reshape her into something more marketable - she just kept being herself. Not as a strategy, not as a brand play. She kept being herself because she did not know how to be anyone else, and she did not want to learn. Every major success in her career, from the original Bobbi Brown Cosmetics line to Jones Road to the hotel she built with her husband, came from the same place: solving a problem she personally had, making something she personally wanted, and trusting that if it was real for her, it would be real for someone else too. The products that failed, by her own admission, were the ones where the idea was abstract - disconnected from her own life, born in a conference room rather than a bathroom mirror. For someone my age, swimming in a culture that screams at you to optimize and strategize and reverse-engineer what the algorithm wants, hearing a woman who has built and rebuilt billion-dollar brands say that her only real method is make what you know and see if anyone else wants it - that is the kind of thing that rearranges something in your chest.

What makes that conviction possible, though, is something Amy named during the conversation that I think applies far beyond makeup or fashion: to have a point of view, you must be comfortable with other people not sharing it. This sounds obvious when you read it, but is remarkably difficult in practice, especially now, especially when you are young and the feedback loop is instant and public. Bobbi’s refusal to make contouring products when the entire industry was drowning in contour kits was not stubbornness. It was a point of view - she did not believe in it, she still does not, and she was willing to let an enormous wave of market demand pass her by because it was not hers to ride. Jones Road’s entire identity was born from a fantasy she described on the episode - what would it look like if Phoebe Philo called her and said, let’s make a makeup line together? Minimal, human, almost bare. And the willingness to launch that into a market obsessed with full-coverage everything required a kind of comfort with disagreement that most founders, most people, do not have. The thing about having a point of view is that it automatically means some people will not see it your way. That is not the cost. That is the proof that you actually have one.

And yet having a point of view is only half of it - sustaining one, across years and decades, requires something else entirely. There is a moment in the episode that I keep coming back to, where Amy observed that the people in their industry who have had real staying power - decades, not seasons - were not the ones who were out being fabulous. They were the people who went home for dinner. They were organized. They were grounded. They were, above all, human first and professional second. Bobbi talked about leaving shoots early because she wanted to be home with her family, knowing it was not the cool thing to do, knowing the other people on set stayed until eleven at night, and not caring. For my generation, I think there is a version of this that manifests differently - it is not always about family, but it is about the pressure to perform a lifestyle that signals success rather than actually living one. The people who last, in any field, are not the ones who look the most impressive from the outside. They are the ones who built something real enough to sustain them when the audience is not watching.

If staying power comes from being grounded, then momentum comes from something even simpler - the willingness to just start. Bobbi talked about meeting people who come to her with a beautiful pitch deck, a funding strategy, a five-year plan, and no product. She does not understand this. Her hotel started with her and her husband shopping for furniture at Home Goods before they even knew the dimensions of the rooms. Amy told the story of the man at the American Club in Hong Kong who overheard a debate about whether to write a three-year or ten-year business plan and said: you make a product, and if you sell it, you have a business, and if you do not, you do not. When Bobbi ran out of packaging for a product launch, she went and bought envelopes and pink tape and made it work - and that scrappiness became part of the brand’s identity. For anyone my age who is paralyzed by the feeling that everything needs to be perfect before it can be public, this is the antidote: start with what you have, make it real, put it in someone’s hands, and figure out the rest once you know it matters. The planning can come later. The doing cannot wait.

And running beneath all of it - the authenticity, the point of view, the groundedness, the scrappiness - is a truth that might be the most important thing Bobbi said, and the hardest for my generation to accept: there is no silver bullet. She said it plainly. It used to be that you went on Oprah, and your book was a bestseller. That does not exist anymore. So, what do you do? You do everything. You go on podcasts. You answer DMs on TikTok without a script or a blowout. You write a Substack. You show up at your own stores and introduce yourself to strangers. When a TikTok influencer trashed her product on camera, Bobbi did not convene a crisis team or draft a PR statement - she looked into her phone, responded calmly and honestly, and quadrupled her sales, a moment now known as Foundation Gate. None of it was strategy. All of it was just doing the next thing, and the next thing, and the next thing, without waiting for permission or a playbook or a guarantee that it would work. For someone early in their career, building something from the ground up, this is maybe the most important thing to hear: there is no shortcut, and that is actually the good news, because it means the person willing to just keep showing up - genuinely, consistently, without pretense - has an advantage that no amount of funding or followers can replicate.

I walked away from this episode feeling like I had been given permission to do what I was already doing - just with more conviction, and less apology. I think the full conversation between Amy and Bobbi is worth your time, and once you listen, you will too.

Available on all streaming platforms. Listen here: Bobbi Brown for (Almost) Reckless Read the book: Almost Reckless by Amy Smilovic

New episodes every Monday. Part of the Almost Reckless universe from CP Media.

Identifying the grounding color ring of a city is predicated on the notions of: temperature, tone and terrain. The color math by city is one of the most frequented read articles (read here) I’ve written. Why? Because when we travel, it sucks if you show up in the wrong vibe rather than (just) the wrong outfit. The color math applies formulas to logic acquired by experience. In school, when I was taught the formula for something, it was hard for me to digest and apply. When I had formula + rationale, I did much better. But when I could add on a layer of deep familiarity, the kind you feel in your gut, my knowledge level and ability to perform soared.

I think the below will help you feel viscerally what I know by experience coupled with some solid, albeit unconventional, analytics. I’ve taken some key activities we all do, no matter where we reside, and framed them by varied color rings. It’s easy to understand, you’ll feel the vibe. Promise.

And please - I encourage - give me feedback in comments, add places I don’t know, things I didn’t think about. Just don’t tell me I’m wrong, cause this is from my lens. Curious about your pov!

Let’s go:

Dominant excercise:

• Ring 1: fast walk, but make it in a heel.

• Ring 2: a treadmill, controlled and scheduled.

• Ring 3: Hiking or things that require deep breaths in an area where the act of breathing in your environment is not a health risk.

• Ring 4: High intensity aerobics and weight lifting that accompanies grunts and maybe a fist pump.

Weekday breakfast:

• Ring 1: anything that can be held in one hand and eaten during the afore mentioned fast walking

• Ring 2: anything in a bowl: cereal, yogurt with toppings, maybe a soft boiled egg with toast. Parameters are set, utensils required.

• Ring 3: anything in a blender, inclusive of a powdered substance like collagen or creatine.

• Ring 4: anything platable - fresh fruits, eggs, it’s the most important meal of the day afterall.

The Soundtrack:

• Ring 1: Things that thump or carry strong messages- The Strokes, the Cruel Intentions Soundtrack, Kendrick Lamar, Eminem. Or music intentionally ironic to lend perspective like Kate Bush’s “This mother’s work.” In absence of music, you’ve pressed play on the many apps you’ve bought to help you learn Japanese or sharpen your conversational French.

• Ring 2: The “Uncommon Knowledge Podcast”, things found on Siriux XM like The Bloomberg Channel, Nostalgic music (note: this is different for all of us, my Gen 90s nostalgia is different than a Millenial’s early aughts)

• Ring 3: Any songs that have a guitars base- but strummed - not a power picking of chords. Or a tune that allows for singing along - sometimes loudly (and who cares, you’re alone in your car, no ones watching or worse, filming).

• Ring 4: music by groups that have more than 3 men in them, often wearing short sleeve buttondowns and pants with cargo pockets they actually use and that end just below the knees. Or anything involving a steel drum or an instrument exuberantly upbeat like a xylophone, a ukulele, or a glockenspiel.

The greeting:

• Ring 1: (if at all) it’s a cock of the head. Nod down or nod up, depending on the level of familiarity.

• Ring 2: a firm handshake, direct eye contact.

• Ring 3: a soft hug or prayer hands with a quick head bow.

• Ring 4: a slap on the back, maybe even a headlock noogie.

The sendoff:

• Ring 1: Ciao (regardless of native tongue), or just three grey dots that linger for a moment then just simply dissapear.

• Ring 2: “I’ll call you next week” - and they actually mean it.

• Ring 3: “Namaste”

• Ring 4: “I’ll see you at the club.”

Load me up with your comments.

Ciao,

Amy

Will asked him directly what his secret to sustained relevance is. And his answer was not what I expected. He did not talk about reinvention. He did not talk about reading the room or chasing trends or adapting to what audiences want. He said something simpler, and, the more I have sat with it, something far more radical: the time to start your next venture is not when the current one starts to decline. By then, it is already too late. The time to build what is next is when what you have is at its peak.

I have not been able to stop thinking about this. Not because it is complicated - it is, in fact, almost painfully simple once you hear it - but because it runs directly against the way most of us are wired to make decisions. We wait for the signal. We wait for the discomfort, the dip in numbers, the feeling that something is off, the slow fade that tells us it might be time to consider what comes after. And by the time that signal arrives, we are already behind. We are reacting to a decline that started long before we noticed it, and whatever we build from that position will be built from a deficit rather than from strength.

A trapeze artist understands this instinctively.

The act looks, from the audience, like a series of daring catches - a body flying through the air, hands meeting hands, gravity momentarily ignored. But the physics of a trapeze are not about the catch. They are about the release. And the release does not happen when the swing slows down. It happens at the apex - the highest point of the arc, the exact moment of maximum momentum. That is the only instant in which the next bar is reachable. Not a second before, when you are still climbing, nor a second after, when the swing has begun its descent, but at the top, and only at the top. While everything is still working, still rising, still carrying you.

Every instinct in the human body resists this, for at the apex, the bar feels secure. The height is exhilarating and the momentum is yours, so why would you let go of something that is working? Why would you release what is proven - the bar you have tested, the grip you trust, the arc you know - for something unproven, something that exists only as a shape in the air ahead of you, with no guarantee it will hold your weight? The answer is physics, and the answer is also Bobby Flay: because the peak is not the destination. The peak is the launchpad. And the person who mistakes the peak for the destination - who grips the bar tighter precisely because it feels so good at the top - is the person who rides the swing down, and down, and down, until they are hanging from a dead bar with nothing left to reach for.

What Flay described, without using the word, is a practice. Not a single courageous decision, but a rhythm - a trained willingness to open your hands at the moment they most want to close. He has done it over and over, across decades, developing the next show while the current one is still pulling numbers, building the next concept while the restaurant is still full, reaching for the next bar while the current one is still at the top of its arc. And from the outside, it looks reckless. It looks like someone who cannot sit still, who is never satisfied, who does not know how to appreciate what he has. From the inside, it is the opposite. It is someone who understands, deeply, that the arc always comes back down - not because something went wrong, but because that is what arcs do - and that the only question is whether you will have somewhere to go when it does.

I am early enough in my own career that I am still figuring out what the peak even looks like, still trying to understand what “working” means for the things I am building. But I recognized something in what he said, because I think, without having the language for it until that night at dinner, it is how I have been operating - maybe not out of wisdom, but out of instinct, or restlessness, or some inability to look at a thing that is going well and not immediately wonder what else it could become. We are never stagnant at CP Media. We are always building the next project alongside the current one, always reaching for something before the case for reaching has become obvious. And I used to think that was a flaw - that I should learn to sit with something longer, to let it breathe, to stop moving. Hearing Bobby Flay articulate the logic behind it, from the vantage of someone who has been doing it for thirty years, reframed something I had been quietly questioning about myself.

The trapeze does not reward the person who holds on longest. It rewards the person who knows when to open their hands - at the right time, from the right height, with the right trust that the next bar will be there because they built the momentum to reach it. The audience gasps at the catch. But the artist knows the whole act lives in the release.

And the release only works from the top.

The Grey Area is where Gen Z talks about the stuff that doesn't have clean answers — business, culture, identity, and everything in between. New episodes every Monday. Part of the Almost Reckless universe from CP Media.

I must have heard her say some version of this on hundreds of occasions during our time working together, and every time she said it, it held validity. She owned that sentence and the information that it held—and everyone knew that she could be relied on as a trusted source of accurate information. I wanted to be relied on as a trusted source of accurate information, too.

One day, Amy asked me a question about a process we were ironing out for an upcoming project. I began to say, “Well, historic-”, and before I could let the words finish spilling out of my mouth, Amy stopped me.

“What do you mean, ‘Historically’?”

“Well, I just know that in the past we-”

“But what do you mean by ‘in the past’? You weren’t there.”

I remember so vividly how I felt in that very moment—like I had been found out. Like the jig was up, she saw right through the professional facade that I was so painstakingly trying to portray. Except that’s not actually what happened; Amy is the one who hired me in the first place, and she knew that I was fresh out of school and didn’t have any prior experience. It was me who I was miserably failing to fool—not her. Humbling.

It was this very moment that I had to look Imposter Syndrome in the eyes. I think that just about anyone can relate to some version of this experience, no matter what age or stage of life you’re in—you walk into a room, you look around, and slowly (or quickly) realize that everyone there knows more than you do, so you fake it till you make it. Or, like me, you fake it and don’t make it—at least, you don’t make it in the way you thought you would (in the grand scheme of things). But can I let you in on a secret? As someone who was very recently let in on this secret myself?

Once I became friendly with the three words that scared the living daylights out of me (“I don’t know”), I began to make it to the place that I was actually meant to make it to—not the place that I was trying to fake it to. And while I’m very much still on this path, I’d like to believe that the outcome starting to materialize is much better than the alternative.

In discussing this very topic on a recent episode of The Grey Area Podcast, a realization hit me. I spent years arguing with my Imposter Syndrome to find out that it might not be the enemy I thought it was—it’s certainly not kind or tender by any means, but if you learn to decode what it’s trying to tell you, if you try to understand it, you might find yourself thanking it from time to time. On one hand, it was the perpetrator of anxiety and insecurity at seemingly the worst possible moments, and on the other hand, it’s the very thing that catalyzed so many monumental shifts in my career—shifts that have made me a better employee, friend, and person. Ah, the classic “frenemy” trope. How sweet.

I think about the sheer amount of effort that I put into trying to emulate someone else’s path, and the never-ending well of frustration that came with it. While I believe that I’m too young to have regrets yet, I do wonder where I would be if I redirected that effort into figuring out where I was supposed to be headed. Walking a mile in the wrong pair of shoes can give you blisters. And now that mine are starting to scab over (this sounds gross, but I mean it in a nice way), I want to share two things that I didn’t know then, but know very well now.

1. When you admit you don’t know, and become comfortable with admitting there is a gap between you and knowledge, the path to closing that gap becomes oddly clear.

2. If you listen to your Imposter Syndrome rather than succumbing to it, it can actually serve as a guide leading you to where you’re meant to be, rather than where you’re trying to go. Lean into what you do know, and seek out what you don’t.

If you read this nodding your head along the way, and I’m speaking especially to my fellow Gen-Zers, I encourage you to read Amy’s new book, “Almost Reckless” (buy here). I can speak to this experience only up to this point—but this book offers insight over the course of decades, from someone who rewrote the rules on finding your own path. Having worked for Amy for the last five years, I can speak from personal experience that the principles in her book check out in a super real way—many of them played a major role in my own professional development, before they were ever bound in a book: the sooner you learn to identify what success means to you, the sooner you figure out how to codify what your principles are, the sooner you’ll be on the path that’s meant for you—even if it makes sense to no one but yourself.

Stella, I have to add my thoughts here. My POV, ok? - Amy

There’s a saying that when you are hiring a sales person, you should always look to see what type of car they drive. What they’re driving should be a grade above what they can afford. Why? Because it means that they’re striving for the next level, they’re hungry. If they’re driving a clunker, they settle; if the car is a huge stretch, they’ll cut corners. I find that the hallmarks of a great team member, every time, is that they’re a bit of an imposter of sorts - we all are striving for the next level. They think they’re just a little better than they actually are in that moment (confidence), they say things they regret (enthusiasm), and most importantly, they recognize when they don’t know something (humble). Clearly, to have all three in play, one of these things will always be compromised. And that’s where a team member that is principled, logical, clear headed excels - it’s a dance, moving forward and backwards, some missteps, some big strides. Moving together to the same beat, or shared objectives, as it were.

Amy and Jeff grew up twenty miles apart outside Chicago, married partners who came to America from somewhere else, and built their businesses on the same philosophical scaffolding without ever comparing notes. They get into the personal constitution Jeff wrote at twenty-three and still reads every morning, the difference between first principles, opinions, and tactics, why the burnt edges are what make the steak taste good, and what it actually means to reduce - to distill a life down to the ingredients that matter and refuse the rest. They talk about the trap of storytelling, the gap between incident and reaction, the kind of leadership that refuses to be efficient with people, and what is gained by walking forward instead of looking back. It’s a conversation about joy as a discipline rather than a disposition - and about what happens when two people who chose to reduce land at the same table.

To see more: Jeffrey Saad for (Almost) Reckless

People ask me what age demographic we design for and if we make things for younger or older customers. Know this, when I say “people” I mean either editors or other fashion industry professionals - especially marketing or branding consultants. You know who never asks? The people who wear my clothes. Or simply Creative Pragmatists. Here’s why. Because every morning when they’re getting dressed, each time they’re considering a new purchase, they’re critically thinking rather than thinking critically.

Here’s the difference. Critical thinking means they’re applying their experiences, their current situation, and their preferences to weigh out what is best for them, right now and for the future. Thinking critically means you’re fixated on a varicose vein or worse, someone elses. I say worse because no one wants to be a judgey little MF.

I’m a big fan of applying reason to the reason why we do things. In case you haven’t read it yet - Almost Reckless (here)- my new book helps you break this down, with how to/action steps, and apply it to all the areas that reside outside your closet. Your career, your family, your happiness and ambitions. And if you’re like me, they’re all deeply connected and one and the same.

So how do I view dressing your age? I don’t. Here’s what I mean - if you view age and clothing in isolation, then you could look at this and think here’s your directive for age 20, 40 and 60.

But the thing is, these are three different individuals entirely, in terms of their personal style. And since personal style is an amalgamation of everything here below, I can state that hot pants here on the left should never succumb to lounge lady on the right - and someone with those loungey inclinations would have felt deeply out of place at age 20 in the shiny shorts.

So image 1 here. Can you tell her age? If I zoom in on the college paraphanalia, I’m going to guess around 20.

Or this one here. She looks straight up to me like the new version of Working Girl. That late 20-something on my subway ride, WSJ hanging out of her bag, eager to get stuff done. This is my lens, anyways.

And now here- she could be anywhere from 30s to 40s (again, my lens)- we go from the bride on a honeymoon, the navigating a wardrobe while pregnant, and having the perfect item for sticky, clingy hands.

And here we find ourselves, the kids are a bit older and we’re standing by the sidelines at a soccer match. The plaid shirt and sandals have all the chill for a busy mom in her 40s. And on the right, they kids have now fled the coop - and the pants that did all that hard work is now the one that is worn when our other 50+ group comes over for my whipcream vodka signature martini.

And now I’m approaching 60, and I’m headed to exercise class - no longer in search of the hot body but rather one that has enough muscle to strengthen bones that have gone to shit.

And here I’m imagining my life in my 70s and 80s. My brain doesn’t have to expand too far, I pick up these ideas from the incredible women I get to meet everyday now - whether IRL or in my DMs. I’ll be on the boards of various companies and get to talk about some things I’ve learned, what I know - but I won’t have to write up anyone’s reviews and for that I’ll be so damn grateful. And hopefully if I’m lucky I’ll have some little grandkids putting their sticky hands on top of the stains I’ve lovingly kept from so many years ago.

So you see, age? It’s not a thing, not when it comes to clothes.

Here’s the beauty of critical thinking. You really begin to question the rationale for things. Why would I be limited to (xyz)? Why wouldn’t I wear what I feel great in? Why on earth would I let someone else’s limited view of age limit my own?

Now, getting back to Almost Reckless…..

you can see how thinking about ourselves and our style through this lens overlaps in to real life. Because as I mentioned earlier, these questions about age come about from those within my industry. Which has me thinking, exactly what industry am I in? I know the answer to this now, and it’s amazing when you figure it out. Almost Reckless helps you get to that point, promise.