The definitive guide to personal style: “Moms” Edition.

Part 1 of a series that I don’t yet have a final number for.

Part 1.

The year was 2009. The time frame for me is important, because it was BCP (Before Creative Pragmatist). Meaning, before I’d figured it out. I was taking my son to some thing or other and he said: “can you just please dress like a “fun mom” today?

I’m going to show you here, in this series, how to do that. Not how to dress like a fun mom, not outfits for the playground, the birthday party or the school function. But how to compile the right ingredients to buildout your style, the style that keeps you moving through life feeling like yourself. Once you become a mom, you tend to either or hold on so dearly to the “former you” that you forgo pragmatism in the times when you really need it the most or bifurcate your style,Time with kids, doing the things you do, often in a style that is alien to you. Mostly because you’ve simply never been this person before. There are the times where you are “you” - at work, at parties, and in my case in sometimes carefully posed fashion photos that could imply that my only reality is backstage at a runway show, at a Polo event, or a magazine spread of “just a day in my life at home with my boys”.

The carefully styled photos of a typical day with my sons:

But here’s the reality of the fashion challenges I faced. What exactly does the person above wear, when these moments are blips, far and few between? When the true picture looks more like the ones below:

So the key word here is “fashion.” Because it’s not discovering what “outfits” work best at hockey practice, the school play, taming the cousins, biking, tennis tournaments, fishing, golfing, camping, boating, hosting the birthday party….It’s about knowing what elements you need to have in your closet that will conspire to uphold or form your personal style thru-line. Not in an attempt to “look good” - though who doesn’t want that? Rather, it’s the pursuit of feeling like yourself - no matter where you are. And since the person now standing on a wet field wiping tears off the son’s face who has just lost his soccer match is the same one who maybe has just had a great intimate night out with her partner, or figured out something really smart and difficult at work, you can see the conflict.

It’s something I address in my book The Creative Pragmatist. When you say someone has “great personal style” you are referring to someone who, every time you run in to them - the grocery store, an event, etc. - they just look like themselves. It’s not a label bestowed to someone whose outfit you admire at an event. Because you can’t give them this label until you know how they show up in different moments of their life. If Audrey Hepburn had been just that one dress from Sabrina, the conversation would have only been about the perfect “fit” and Givenchy. But Audrey’s throughline of personal style confirmed that was no one hit wonder. She knew who she was and how to convey it visually.

The Creative Pragmatist is a thinking book because Personal Style can be learned, but learning requires thinking. See how that works? There’s no such thing as 7-minute-abs and there’s not a phrase or 3 steps that will create your style or change your relationship with clothing. At the same time, it’s not Tolstoy’s War and Peace. In the book, I outline the steps clearly, and I know that’s changed lives. Because thousands have told me so. And that statement isn’t a stretch - because while dressing well is nice, knowing who you are and how to visually convey it, feel it, and live it every day is life altering.

So here, specifically, I will talk to the moms. I know what you’re going through and I can help.

First, I’m going to layout the Mom tropes. And here’s the thing, while it is funny to laugh at the tropes, reality is that in some way we all want to be a little bit of each of them. Just not to the point that it’s so easily encapsulated here.

BUT FIRST, I NEED TO SAY THIS - for this article, I tried to find images of these “tropes”. And I did, but I didn’t feel good choosing any of them. Because I know people who are these “tropes”, and they’re all phenomenal people. And some aren’t. And if they aren’t it’s not because of their style. So don’t let the bigger point get lost here - this isn’t about how we think about people because of their style, it’s about how we think of ourselves when our style doesn’t reflect the scope of who we are.

There’s a reason why we don’t want to be described in such easy simplistic (and funny) terms. Because it’s a bit one dimensional. It reduces you to well…..a trope. And that’s not how we want to be. “Creative Pragmatist” was formed on the bedrock of knowledge that we are many things at once, that we have depth as individuals, and that a thruline of our style dna, our 3 adjectives, keeps us grounds us but never sinks us.

Ok, on to some highly practical advice. I’ll show you a key investment piece and why it makes so much sense. Note that the WINSLOW PANT is rooted in the Creative and the Pragmatic and it manages to be chill, modern and classic - all at once. When you become a mom, the creative side doesn’t change, but the pragmatic considerations do. With the right core elements, this simply becomes a puzzle of styling rather than a full out overhaul of a closet.

What to look for in the perfect Mom pant:

1. Can options happen when it’s hacked? This can be shortened, ballooned or left long. All quick styling hacks that give major range of vibes.

2. Elastic waist but not heavily gathered- no junk in the front of your trunk moments. Stretch, ease but still clean - almost tailored like.

3. Modernity - it’s a classic and chill in that it’s a sweatpant, but the sculpting makes it modern, but the pliability of the material keeps it from being ridiculous.

4. Clean seaming- if you buy a sweatshirting pant that is overly washed or with raw seams or heavily topstitched , then it is heavily emphasizing the CHILL aspect - but bcs this is already elastic waisted, in sport material the chill is there - all those other details make it too onesided. Clean seams give a tailored vibe, polished - this gives you options and why it looks great with a blazer or a sneaker.

5. Drawstrings that are on the INSIDE - if they are exposed on the outside only then it will definitively always read more casual. Limited options.

So you see below, the range. For a photo shoot we put extra C to the Creative Pragmatic. But whether you are at playground, tennis tournament, golf tournament there’s no sacrifice when you need to lean harder on the P. The olive color here and the red one Here are perfect.

Ok, more to come. This is a lot to absorb, and already from what you’ve read I’m sure you can apply the bigger concepts across a wide swath of what you already own.

In the meantime, PSA for some of our stylists that are moms and incredibly helpful on their insta: darianne.tibi; keturah.tibi; acacia.tibi; lees.tibi.

More to come. Please comment on what else you may be looking for, I’ll try and help. Ok?