First dates inspire a low-level nausea and roiling dread for a variety of reasons. It could be horrible or it could be amazing. Meeting a stranger at a bar contains a world of untold possibility. Maybe they’ll be your soulmate, someone that makes your heartstrings zing and your loins quiver. Maybe they’ll be the worst person you’ve ever met in your life, and you’ll be better for knowing that someone out there that horrible exists, and just how to avoid them. Or, maybe it’ll be a perfectly average night, nothing to write home about, but just a two hour chunk of your life in which you sat across the table from a perfectly normal dude with a beard in a nice button-down, who you didn’t really have chemistry with. Whatever. You play the field for as long as you can until something that clicks comes along.
There are so many factors that go into the first date, from picking the venue to deciding what to order at the bar. All of those things are fine, game-time decisions for the most part, but there’s one thing that’s pre-planned, something that you actually really think about — your outfit. Yes, a date should be about the charming repartee and your stunning wit and whatever else you bring to the table, but the sad fact of the matter is that people are shallow. I once had a friend tell me that she refused to go on a second date with a man wearing loafers with no socks. I’m not here to tell you that you should be super concerned about whatever it is you put on your bod. Any good person will like you for you, not for the weird bandage skirt you squeezed into and are counting the minutes until you can take off.
But, clothing kinda, sorta, maybe matters. Maybe. Just a little. In the words of the inimitable RuPaul, “Don’t fuck it up.” Choose what you wear wisely. Here’s a few potential first date outfit types, and what they say, in ridiculous, overarching, generalized statements, about you.
1. Anything that is a personal fashion risk, be it a crop top, hot pants, stripes when you only wear florals.
Every morning, before you leave the house, you take a long, hard look at yourself in the mirror and whisper quietly, “I’m going to kill it today.” You pride yourself on tweaking situations that should be easy and making them just a little bit harder, like a personal challenge you set for yourself. That neoprene crop top that you impulse bought at H&M the other day makes you feel a little daring, while totally confident. Honestly, you don’t need anything else. You’re probably fine.
2. Your boring, weird business casual slacks and a silk blouse because you didn’t have time to go home and change.
You make a lot of to-do lists — they’re papered all over your apartment, on the mirror in your bathroom, on the back of your front door, on piles of mail sitting on your coffee table. You make these lists because they impose order, but you rarely check anything off the lists. The process of simply making the list makes you feel better, and so you continue, writing down things like “toilet paper” and “pay student loan bills” on the backs of those subscription cards that fall out of magazines. You’re no-nonsense. If you have a first date, you at least wear your nicest blouse and maybe remember to put on lipstick, but really, running out the door from work to this thing is just another part of your day. NBD.
3. Something you’ve agonized over for at least a week, carefully picked out and tried on numerous times.
Dating is new to you, either because you’ve never really done it, or because you’re emerging out from under the long shadow of a long-term relationship that finally hit its expiration date. You’re probably not sure how this date is going to go, but you’re 100 percent positive that every single item in your closet isn’t going to fly. You’re a consummate planner. You lay out your clothes every morning before work because otherwise, you’ll find yourself standing in your underwear in your bedroom, staring at your closet, overwhelmed and stymied by the choice, late again.
4. Freakum dress, regardless of the date activity.
“Why don’t you take this seriously?” your mother asks you every time you’re on the phone. “When am I going to have a grandchild?” This conversation, which comes like clockwork after Bikram on Sunday mornings, is consistent and nagging, like that one mosquito that somehow makes it into your room at night that you can never catch. The freakum dress is your first date calling card, something that keeps you top of mind, but also something that makes you feel really, really great. You wear it because you’ve worked hard on the body you were given, and because you want to make an impression that beams confidence. You order whiskey at the bar maybe because you read somewhere that it makes you seem cool, but also because you really like the way it burns a little going down. Secretly, you want to please your mom. You’d get married sooner rather than later if you had your way.
5. Your go-to “date” outfit.
Dating is a numbers game, something that you have down to a science. You have a choice of three bars or restaurants that you always pick, a drink that you order, a set list of topics that you avoid. The nightly OKCupid search is sandwiched between rigorous applications of eye cream and watching the opening monologue of Jimmy Fallon. You’re unafraid of success professionally, but have found it elusive in dating, and despite the fact that your go-to karaoke song is “Independent Women” by Destiny’s Child, you still have a secret Pinterest board full of wedding dresses and floral arrangements that you update from time to time.
6. Whatever you feel comfortable in.
You’re normal. You are completely normal. This is the only way to be.