What do I wear when I know I’m going to run into an ex?

Feelings math presents: how to build a confidence formula

Jun 29, 2021

This month, I’m donating to Uniquely You’s scholarship fund. Uniquely You was founded in 2010 and is led by Shaleah Lache Sutton (also a twin parent!), for the stated mission to help Black girls discover, define and become who they are through various programs including a summit, summer camp and the stated scholarship fund.

You can donate by clicking here!

The below is a dispatch on how to get dressed when you might run into someone you’d like to make an impression upon that is far more wholly wrapped up in your own sense of confidence than it is in their perception of it/you. In other words, just the regular, everyday motion of thinking, “What should I wear?,” etc.

It’s a spectacular night, right?

And you’re going to meet some ~friends~ for a ~drink~ at ~the bar~ or maybe you’re actually getting ~tacos~ and everything seems like it’s going to be so much more fun because of the squigglies you’re putting around your plans.

There’s a possibility that the artist formerly known as your partner, or just like, a person who has been exposed to some pretty fucking intimate parts of you might be at the squiggly place (or maybe, actually, it’s anyone to whom you just want to convey that you’re doing really well who will be at the squiggly place) and you’re kind of excited, or really, you’re more like riding high on the thrill of knowing, or thinking, that you might see this person and that you have time in advance to prepare.

You have time to prepare! You can write a speech (“To whom it may concern, I’m fine, thank you!”), or more covertly, you can choose an outfit that precisely conveys in no clear terms how great you are doing, etc, so, what do you do, what do you wear?

The answer is not satisfying to the extent that it is a formula, not an actual prescription (how can I actually tell you what to wear in such literal terms! I don’t even know what you look like, much less how you feel, what gives you confidence, whether you prefer a v-neck to a crew!) and the variables of the formula totally depend on your preferences.

I’ll lay it out as clearly as I can using myself as a proxy:

If you’re just here for outfit credits and comps, scroll down to the last picture

Here, for example, is what I would wear. This outfit might seem profoundly uninteresting to you. It could be the antithesis of what you would choose and frankly, that’s my favorite thing about style: It’s a metaphor for being human.

It’s like, we all feel feelings, but the way they present, or how we enact them is so super different person to person. That’s why the formula thing seems much more sustainable than prescribing actual clothes. To get to the equation, here are some questions you’d ask to build the base of the look:

What is your style comfort zone, e.g. what is the no. 1 garment you feel good in no matter your mood at the moment? My answer is ~the button down shirt.~
What is your favorite body part? Like the one you are most wont to accentuate through dress? I rly like my legs — hence the tiny shorts, or underwear, really.
What is a style risk you have recently taken that actually paid off? My answer: wearing briefs as shorts and spending the day-into-night out without once wishing I could go home and change. (You know it paid off if you don’t want to change, you also know it paid off if you want to take the same risk again/it no longer seems like a risk.)

Then you use the answers to put the formula together:

Comfort zone + Accentuation of favorite body part x Risk I have already taken, which paid off = What to wear when you’re going to run into someone and want to convey that you’re doing great.

Now here is the logic:

Comfort zone

You include one part comfort zone because this is the reliable, durable, sure-fire thing that you come back to over and over. The garment that makes you feel the most like yourself (like, the good version), that you wear so often you’ve become intimately familiar with how you look (feel) from every angle while in it. How it works, when it works, and just as importantly, when it does not. You’re so close that it’s almost always just like, a hug. And that hug is key! Because considering it, you nail two important qualities within the comfort zone piece in that (1) you look good by your own standards, absolutely, but also (2) if and when the perpetrator of belly-butterflies is to make you feel uncomfortable, you have on your hug to hug you. Do you know what your comfort zone piece is?

Accentuation of favorite body part

Pretty simple: you include a garment that flatters your favorite body part — this can be anything! Nail beds, hair, legs, belly button, the birthmark on your shoulder because a) why the fuck wouldn’t you wear something that further underlines something you like about yourself, b) if you don’t know what this thing is yet because you’ve never thought about it, why the fuck wouldn’t you take a moment to think about it?, c) within the realm of further fuckers: why the fuck wouldn’t you then want to remind yourself that you’re making a conscious choice to acknowledge this part no matter how self-deprecating you may be in other areas of your body (life)?

Now wear the damn thing! You’re fucking beautiful! Genuinely, I’m not just saying that.

Style risk you have taken, which paid off

The most elusive part of the base formula is also the final part: a style risk you have already taken that actually paid off. What is a style risk? That thing where you put something on in private, which makes you feel like, “damn this is good!” The risk element is your not being sure whether you’re confident enough to wear it out, but taking it for a spin in the public square anyway. How do you know if it has paid off? When you think you’ve succeeded to add a new layer of depth to the shape of your style, or in other words, when you say to yourself, “I’d totally do that again.”

This, in my view, is how to build fashion confidence: through the trial and error of taking small style risks. Often they don’t work, which can be kind of deflating, but on the bright side, “it’s just fashion,” so keep iterating until they do.

Finally, there is the fanfare:

Or in other words, the accessories. The details. The quirks that add a cherry to the sundae of your base look.

These elements are more technical, so I can walk you through how I thought of mine, but they are going to change depending on what comes out of your writing a confidence formula.

Shoes: With shorts so short, I stay away from heels (less desire to elongate leg) or shoes that are too open-foot (again, less desire to elongate leg). The shorts are also flimsy, and sometimes a closed-back flat is too harsh (big elderly gentleman in boxers and tuxedo shoes energy, which actually sounds great by description). I’m basically wearing underwear so less — but not too far less! — structure is more. The closed-toe flat mule, with its refined narrow toe and little bow, is a pretty good fill-in, leaving the back of the foot exposed and espousing a sandal vibe even though my toes r in hiding.

The jacket: You never know how high the air conditioning on the subway is going to be. You also never know where the night may take you and tbh, if I were to end up somewhere snazzy, I 10/10 would take off my shirt, wear the jacket as a blouse and either sling it over my arm or tie it around my waist a la:

It’s a good contrast — the embroidered fabric (fancy) with the suede (casual) on my shoes.

Jewelry: Always. One more element of personality to convey that doesn’t actually tell you anything about who I am but does suggest there is lots more to know. A good conversation starter if the person starting the conversation with you recognizes the nuance of what the former phrase means in the cereal aisle. E.g. “Hey, I noticed you’re wearing a ton of jewelry and that it doesn’t tell me much about who you are but I get the sense there is a ton of wonderful stuff to learn and I’d love to hear about it.” Like, take that, ex-person you’re dressed to run into!