<CLOTHES LINE> No Idea How To Dress For First Dates Anymore?
An Advice Column For Wardrobe Conundrums And Other Closet Cases
DEAR DRESS CODES,
I have a few first dates coming up, and it sounds cliché, but suddenly I’m that person with a closetful of clothes who feels like she has nothing to wear. I haven’t gone on a first date in years, and I have no idea how to dress for one anymore. I’m also broke, so please don’t give me a punch list of trendy new things to buy, maybe just some general guidelines for choose from what I already own. — Pathetically Wardrobe Weary
First of all, that feeling isn’t cliché—especially in this current moment when so many of us are still living in our post-pandemic “eras.” There’s a lot we’re still learning to navigate, and sometimes it’s the subtle shifts—like getting dressed/reframing our wardrobes, versus say, newly-adopted habits such as sanitizing our hands and touch-points more regularly—that trip us up more. Honestly, who isn’t looking forward to the post-post-pandemic era when we’ll no longer preface statements with, ‘Since Covid…’? And when it comes to getting dressed these days, the line between our interior and exterior lives is still so fuzzy—just look at all the pants-less celebrities. Our codes for how to dress for work, leisure, school runs, etc. have all considerably evolved, so it only makes sense that you’d be confused about what to wear when meeting a stranger IRL with whom you hope to have some kind of romantic future. WE GET IT. We’re not going to tell you how to dress, but instead offer up a few things to keep in mind:
Broke or flush, don’t go shopping. You shouldn’t have to buy a thing if you already feel pretty good (generally-ish) about your wardrobe, and it’s just a matter of reframing how you look at it. (Acquiring more clothes and introducing even more factors isn’t necessarily going to make your decision-making process any easier—if anything, it might induce the opposite.)
Don’t dumb down your style. It’s always weird when someone dresses really basic and flat for the first few dates, and then shows up at the next one wearing something noticeably more different that reveals their true-style colors. It’s a bit of fashion fakery, in our opinion. You shouldn’t have to psych the other person out, or ease them into your style. If they’re not into how you dress, then they’re not really that into you. Harsh, but wouldn’t you prefer to know that ASAP?
Play = yes. Experiment = no. Don’t use a first date as the moment to test run a daring new look. Just don’t. Here’s the thing: you don’t really know how the date itself is going to go, and that should be the extent of the night’s unknowable/uncontrollable factors. You may end up hating the experience. You may end up abhoring the person you’re on a date with. But you shouldn’t ever hate your outfit, especially when you can control that component. Feeling good about what you’re wearing and how it makes you feel—not just as someone on a date, but as a living human being out in the public world!—could be the one redeeming factor of an otherwise shitty occasion. Maybe your date sucks, but you don’t need to worsen the experience by regretting what you wore.
So don’t experiment, but do have fun. Choose something you’d wear to meet up with your best friends for dinner, and you’re all bringing it—for yourselves and each other. Channel that vibe of a guaranteed fun night out (even if it’s not actually guaranteed), but don’t overthink it. Your date could be a bust, but maybe you’ll lock eyes with someone else across the way. Or maybe someone will simply compliment your outfit. Regardless, your confidence should be oozing from the get-go. Women already spend too much of their lives in service to others, so take this moment to be a little selfish. Dress for yourself.