What should I wear on a casual first date?
Dear...,
What is your name? I didn't catch it. I don't know how this inquiry landed on my desktop, but here it is, and I don't know your name, but I'd like to call you Frank, so if you don't mind, I am going to call you Frank.
Dear Frank! Hello, Frank. I want to be frank with you about the frankness of this question and frankly, I have been in the depths of capital-P-Process for the past two months. I am not naturally a linear thinker, I am, in fact (in frank?), the opposite, and so burying myself in Process, attempting to untangle the wires that make up the constellation of how my mind works but output fails has been...no easy feat! But, I assure you, a rewarding one - and you know what they say, the brain is a muscle and the only way to make it stronger is to ram it against a hardwood surface and yell "Ouch," at the feeling of pain, which any fitness instructor will tell you is the sensation of change. Of progress!
So here I am, learning how to build frameworks and templates for the betterment of tomorrow, deprioritizing the truly important stuff, like thinking about what I'd wear to stand on the sidelines at a marathon in Chicago for which I will not be in attendance (charcoal gray sweatpants, a black crew neck t-shirt, a green jacket with fringe, and something silk to tie around my neck). But I could only neglect what keeps the rubber ducks of my bathtub afloat for so long so when this query arrived, dressed to the nines in concern about what to wear for a hot date. So I turned the templates off to think about The Real Stuff but you know what I found?
More templates! I am often asked for outfit advice on what to wear on a casual first, or second, or third (or basically any number date where you are not yet comfortable enough with the other person so you feel you want to ask someone else what you should wear). In the past, I've always offered pretty literal suggestions, like leopard prints, or an argyle sweater ( I actually think I offered these together), but those recommendations can only go so far. At the risk of sounding like I run a VC-backed startup (I don't), that kind of advice doesn't scale. So, you know, now that I'm a template person, I have been thinking: Can I build a template to help you figure out what to wear on a first date? Can I, dare I suppose, be the template?
I'm just kidding, that's not a thing. But here's a stab and several templates, categorized by garment types because those who like short things are not often those who like long things, and those who like dresses are not always those who like jeans and those who like pineapple, often recoil at... you get the point. So let's just go, ya?
I recommended a pair of shorts, but a mini skirt ( or skort!) works too. I'd add socks so you can feel like you're wearing boots to the extent that they ride up to about mid-shin, but there is something more dynamic about loafers or a pair of brogues. Maybe it's the two layers instead of one. The shirt recommendation is arbitrary, but I would recommend something long sleeve; it tends to offset the shorts, and adds balance against the socks. The jacket can really be of any sort-trench, utility, wool. I like it when they're the same length as the shorts or skirt, but you do you. Alternatively, btw, you could wear a mini dress in place of shorts or a skirt, and a sweater over. But now we're deviating from the template....
Knee-high boots are the shoes of fall, and probably winter, and we're still early in their life cycle so honestly, even though I am deeply invested in wearing them (ankle boots just don't feel "right" anymore and I have always basically hated pairing all shoes except for sandals with jeans), I'm not sure how to wear them and nail them quite yet, my mind keeps taking me to a denim shirt, high waist jeans, and a pair of kitten heel boots, so that's where I took you. What do you think of the air pressure?
Is it considered a faux-pas to recommend a pair of sweatpants for a date? If you're going to the movies, or bowling, or to dinner at your favorite neighborhood "joint" (I have always wanted to be the kind of person who uses this term in earnest to describe a dining facility that I frequent), I think it's worth trying to tuck an "inspired" pair into flat knee-high boots ( this pair of $800, and I'd say it's worth getting a solid pair that you are confident you'd wear into the ground, but $800 is $800, so maybe, some of these second hand are a good option, LMK). Add a cardigan, and an ascot. You're basically Princess Diana now. Included an evening clutch as such, btw.
I'm not a dress person, I don't think, but if I was one, I'd likely wear some version of a tunic/caftan with a turtleneck under it and shoes that could qualify for on-stage dancing with stars, but also holding hands under stars, if you know what I'm saying. Add socks, don't add socks, Pull a cardigan over the whole enchilada and belt if you please.
Graphic by Dasha Faires. You desire a one-and-done approach to getting dressed to look ~and feel~ like you. I get it. You're a grown-up. I think I'm becoming one too. Sorry about the shoe choice, you can choose your own adventure if sandals after labor day are v much not your thing.
I offer just this in addition: your outfit is only as good as your outlook, which I know you know but which could stand to be reiterated, so grab that date by the horns, you show that motha fucka that you put the fffffffffffffffffff! in fun and if shit hits the fan, or you simply, amicably decide you are not a match, figure this: time is young, and you look great, so keep your head up on the commute home. Chef's kiss, wink, nod, mwah.
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