Outfit Tutorial: How to Make Your Former Style Feel Like Your Current Style

Have you ever experienced the feeling of outgrowing your style? I have made the mistake of misinterpreting this sensation as a declaration that my style is not my style anymore but I think it’s really this expectation that by now (as in, the time at which you believe you’ve really reached adulthood), it should be different.

I have called this “phenomenon” a number of things such as de facto outgrowing your style, palate-cleansing, evolving into “thoughtful” personal style, or most recently: streamlined fashion but all of these pleas have danced around what today I will call the truth, but which tomorrow I may rescind: my style isn’t actually changing, it’s just… maturing.

That’s a significant word swap, and I’ll tell you why: when something changes, it’s no longer the same. When it matures, however, it is, at its core, still the same thing, it just has more perspective. It’s expansive. Like us, you know? As we grow up, we don’t actually change, we just settle more firmly into who we are and throw away the things that perhaps we have tried, but have never actually been true of us.

I realized this right before the holiday break when I came to work in a blouse with a ruffle collar layered under a cashmere v-neck sweater paired with high waist skinny jeans and black suede Adidas sneakers. Someone commented that it was funny to see me in sneakers, which took me by surprise because they’ve been a relative mainstay of my style for as long as my style has been conscious. I may not have known the reason for their presence–that I consistently pursue tension in how I dress (e.g. formal trousers with casual shoes; fancy footwear with athletic apparel and so forth), but it occurred to me that I hadn’t worn sneakers in a very long time. When I dug into why, because, you know, I love a feckless intellectual investigation (I think some people call this navel-gazing?), I realized that after I turned 30, I started to feel like I was trying to act young and hip every time I put on three kinds of garments that I’d defined as uniquely me throughout my 20s. Said garments were:

Leggings (see: this feature image)

Utility jackets (see: same feature image)

And sneakers.

So, mostly, I eschewed them. I’d like to think that overwearing such items while I was pregnant contributed to the shunning, but I think fundamentally, what I wanted, really, was to be taken more seriously. And because I didn’t honestly believe that I deserved it, I used clothing (kitten heels and straight-leg jeans and shirts tucked into them and trousers) to try to make it be true. Maybe the greatest lesson of my very early 30s has been this exactly, but lately I have found myself nestling more comfortably back into the “old me” clothes, just in a new way. So the good news seems to be that I now believe I deserve to be taken seriously. The bad news is that you’ve read 534 words, but I’ve yet to make good on the titular prompt and you still have to withstand how I’m wearing old me clothes in new ways. I guess you can leave if you’ve run out of time, but if you’re sticking around, I’m here toooooooo. No more ado, here for you:


A good question to ask yourself is: what would the most cliche version of me wear this with ballet flats — or better yet: what would I never wear with ballet flats because it’s too cliche? The answer for me is an outfit like this one, boasting a very mature buttery leather brown jacket — back-office brown! — with a silk blouse underneath it of the same color and a pair of jeans so tailored and stiff not even the most effusive attempt at a squat will get me very far. For jingle bells and flair, I have also included pearl earrings, wayfarer style sunglasses and a bag tiny enough to hold just the essentials of a self-assured woman.


Same question applies, but the subjects change. The most cliche way to wear leggings used to be to work out or weekend schlep, but in 2020, they’re a closet mainstay, so maybe this plea is cliche too but for the purpose of this exercise, I added mary janes with a comfortable heel, a white Hanes ribbed tank and tuxedo jacket so technically I could be: going to a gala, to work, or, you know, to weekend schlep. But I don’t look it! Or do I? You decide.

Army jacket

The first utilitarian garment I ever fell in love with: Army jackets defined so much of my style through the early to mid 2010’s and then by the end of them I started to feel like a parody of myself every time I put one on because I couldn’t shake the way I used to wear them — with something cutesy like a floral silk top and high waist denim cut-offs and ankle socks and brogues. I actually didn’t nail the new me in old army jacket until I was styling this story and said to myself: Okay, what would I wear on a Monday to work if I knew I had two meetings out of the office, and might be going to like, a presidential candidate fundraiser at night? I landed on this Toteme top styled over a black turtleneck and these wool pants I got from a sample sale with black kitten heel boots then put the jacket over it. So I guess the question part of this tutorial would read: what would you wear right now for an event that reflects the “new you,” and can the jacket fit in?

The spoiler answer is that if you have a flexible enough mind, it’s always yes.

Sooooooooooo, what are some clothes that are “so you,” but which could use a resuscitation? Tell me.

Maybe I can help.

Ta ta.

(For now.)

Photos by Sabrina Santiago.

Leandra M. Cohen

Leandra M. Cohen is the founder of Man Repeller.

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