How to dress at every age.

Ignore the click bait title and art. This will be thoughtful, promise.

Can you recall the magazine articles, how to dress at every age?

They often took a similar skirt body and showed how it would be accessorized, lengthened or camouflaged as you progress through the years. I don’t blame everyone for having such a mindfuck when it comes to this subject. I blame them. But, alas, blame gets us nowhere - so here we focus on resetting our mind and moving on. Through a series of visuals I’ll show you how as images speak louder than words.

My urgency in writing about this, now, is that I’ve just returned from a trip to San Francisco working with one of my favorite people in the world, Sherri McMullen. We had around 60+ appointments, and if I had to guess the ages ranged from 30-60. And many of them, regardless of where they fell on this age scale, asked me for advice on how think about age appropriateness when getting dressed. And while on the surface, you may believe the idea means something different to everyone depending on their age, there was a clear thru-line when I drilled deeper to the real concern. At first in my probing, I thought I’d found it when “trends” kept being brought up in respect to age. “I don’t want to look like I’m trying to hard, to thirsty, a trend victim.” But if we flip that on its head, we get closer to the real issue, and I’ll summarize it here:

“as I get older, it’s important that I communicate that I know who I am. My personal style is a reflection of that. If one day I am a “mob wife,” an “Italian Maximalist” or a “Coastal Grandmother” then I will project, if to no one but myself, that I don’t know who I am. “

And this clicked and it also crystallized for me why I’ve been not just “meh” but actually annoyed at the Sex and the City’s / “And Just Like That” costuming. And that’s the key word, it became costuming, troping, rather than helping convey the story line, motivations, and a setting of context. A quick visual here, compare and contrast:

The early Carrie, she was given tremendous latitude to experiment. Her outfits conveyed she was deeply curious, opinionated, game for anything. And not ashamed to be figuring it all out, it’s part of life’s process. Each outfit communicated all of these things at once. But the “Now” Carrie became a bad copy of the former Carrie. A literal trope of what it looks like to have way to much funding to recreate exact replicas that never hit the mark. And they miss it because life moves on, the aim is not to recreate exactly what was but it’s in the thrill of figuring out how all that lived life plays in to who we are today. Our better understanding of how we show up as ourselves no matter the environment. Alas, that doesn’t mean a complete disregard to our surroundings. Carrie showing up to a farm to be with Aidan’s kids dressed in 5 inch platforms and satin no longer is about whimsy, it just seems weird she hasn’t figured out how to do “her” in varied situations that call for some - a bit- of understanding/recognition of the terrain/temp/vibe.

While I don’t pretend to have it all figured out, I do stand on far more solid ground than ever. Critical thinking, information, reflection - that will do that for you. Here’s a visual cue to the tropes, the films, the icons that I was too young to have on a Pinterest board but existed in torn out magazine pages or just simply in my memories when I was busy diving in to varied style personas:

It was a mashup, the Preppy Handbook, any John Hughes film, Flashdance, Ally McBeal short mini suits, Kate/Gwyneth/Carolyn, the Donna Karan pantsuit, Plum Sykes from Vogue, Carolyn Murphy and yes, even Carrie by way of the real SJP.

I tried hard for my own interpretations of this growing up. Any that were in my Flashdance /Footloose phase seem buried, and I’m not angry about that.

And so now here I find myself, my older self. And whether you can grab this from photos of me over the years, or in my imaginary younger year’s Pinterest board, the thru-line is there - I can see it in pictures of me now. Chill, Modern, Classic with a twist of humor (in the way of irony, ick, or quite literally).

And this is when you cut down to what it means to dressing your age: it’s about knowing and dressing your style. In other words, yourself. This next visual will help drill this point further. Here’s a recount of a conversation from McMullens:

Person: “You’re wearing the tie-dye jean. But you paired it with a navy sweater, so that it looks more age appropriate, right?”

Me: “no. I paired it with the navy sweater because it now looks like me. Darianne paired it with the striped shirt, I would do that too.”

Person: “But you wouldn’t wear it with a floppy hat and low cut shirt or lots of jewelry, that wouldn’t be age appropriate, right?”

Me: “no. It just wouldn’t be me. Stevie Nicks, she would do that. She’s quite a bit older than me. If you saw her in that, she’d just look like Stevie. At any age”.

Which brings us back full circle now to the original visual. I originally set out to try and “recreate” those visuals from those narrow minded articles about dressing your age. But as I was doing it I realized, I would wear all these things today - but the BIG difference is the where and how it would be styled. I wouldn’t wear the short skirt in my office, it would convey too much of an un-seriousness for me. At least if I was having a meeting that day. And my 20 year old self would have loved the full skirt. I even had an idea to just make the 70+ person ridiculously covered up - but I realized that’s a vibe too - for the right moment.

Now, you see the visuals through a different lens, right?

And we come back to the notion, it’s about dressing like yourself, the one that is tweaked for different environments, activities, or considerations like terrain or culture. Standing out whilst fitting in. Creative, yet pragmatic.

See?