How to Pick the Perfect First Date Outfit: The Definitive Guide for Women

Woman trying on shoes for her first date outfit

I give dating advice for a living, and I studied fashion during undergrad, but picking a first date outfit has always presented a problem for me. I hate picking a first date outfit so much, that for a long time I purposely scheduled dates for right after work so that I wouldn’t have time to go home and change.

Why on earth would I want to wear my office attire to a date when it’s not my usual style at all? Because otherwise, I would totally overthink my first date outfit! I felt like nothing in my wardrobe resembled any of the girly, flirty, semi-conservative outfits I would always see in magazines as suggestions for first date looks.

 It’s ironic because I’ve always dressed in a way that’s arguably a little too sexy, which you may think is something I’d want to wear for a date. But, I didn’t want to give off the wrong message when going on a first date with a guy who might make assumptions. 

 Since using dating apps heavily during my late college years, my style, my self-confidence and attitude towards dating has evolved. I no longer prefer to go on a first date in my office attire, but you definitely won’t see me in the floral sundress and jean jacket combo that every woman’s magazine is suggesting for a first date either.

 Top Tips to Pick the Perfect First Date Outfit
  1. Throw all the first date outfit advice you’ve ever heard out the window

We’ve been programmed to think the perfect first date outfit is meant to look a certain way: flattering without being too sexy or showing too much skin, girly but with a dash of tomboy so that you don’t appear “high maintenance,” and overall, pretty plain and neutral as to not offend any potential date.

I want you to throw that antiquated rule book at the window! Because guess what? If your super high heels turn off your 5’8” date, then he’s probably not the right guy for you. If your spiked choker freaks your date out, you probably wouldn’t see eye to eye on many other, more serious issues.

It may sound harsh, but the way you dress is an important expression of yourself. You don’t want to date someone who wants to change your wardrobe and style. And, you can make a reasonable assumption that your wardrobe won’t be the only thing your date wants to change about you.

  1. Pick your natural style – don’t dull down or dress up!

Even after following step 1, it can be easy to instinctually tone down your usually edgy style or trade your usual jeans for a flirty mini skirt in hopes of winning over a date. But, while we all want to put our best faces forward on a date, you want to make sure it’s your face, not the face of a woman you think is every guy’s dream girl.

Don’t focus so much on trying to make your date like you. Instead, focus on getting to know your date and deciding if you like him and/or if you two are compatible. If you focus too much on trying to get your date to like you (a mistake a lot of women make), you’ll end up putting forward an inauthentic, and probably less interesting, version of yourself. This may ironically result in your date not finding you as irresistible as you truly are, because he’s not getting to know the real you.

Or, perhaps he’ll like the watered-down, dream girl version, and you’ll end up in a relationship where you feel like you’re always pretending to be someone else. Neither option is great. 

By being yourself, you give your date the option to really get to know you and decide if he sees a future, or at least a fun time, with you. And if you don’t vibe? No worries, that frees up your time to find someone that does vibe with your real personality.

Wear something you would normally wear out to dinner with your girlfriends, don’t get caught up in wearing the kind of thing that men allegedly like a woman to wear. Contrary to what you’ve heard, not all men are the same, and if he’s a catch, he’ll want to meet the real you! 

  1. Wear something that makes you feel good

If you’re still stuck on what to wear, focus on choosing something that makes you feel good. Something that makes you feel confident, sexy, and awesome! Chances are, that means nothing that’s uncomfortable or too unlike what you’d usually wear.

This, of course, is different for everyone. I’m pretty comfortable in heels and they make me feel much more confident, so I nearly always wear heels on a date (unless we’re going hiking). For you, this could completely not be the case, and that’s totally fine too. Remember, it’s okay to stand out and dressing to make yourself feel good is the best way to look good! 

  1. Always bring a jacket — and maybe an extra pair of shoes

 While there’s always the cliché of asking your date for his jacket, the realist in me always likes to make sure I bring a jacket on a date. And, since I’m almost always driving myself to a first date, I also have a pair of sneakers in my car.

You never know when a great first date can lead from a casual coffee to a 30-minute walk around the park, and I don’t want to have to turn that down because I decided to wear heels. I also know myself and know that I would cut a date short if I was feeling too chilly — this goes back to wearing something that makes me feel good. If I’m freezing my butt off at the restaurant, I won’t feel good!

Of course, in this vein of practicality, dress to the occasion. Don’t show up to a hiking date in a minidress and don’t show up to dinner in your favorite Lulu Lemon leggings.

At the end of the day, picking a first date outfit is like anything else — practice makes perfect! I went through many years of choosing a more conservative, toned down outfit from my usual sexy, punky style before learning to own it. I’ve also learned to enjoy getting ready for a first date in a pampering myself, self-care kind of way. It can be nice to take time to pretty yourself up and indulge in some pampering spoils. 

And guess what? If you find your magic formula, there’s nothing wrong with wearing the same outfit on every first date you go on. I won’t tell if you don’t…

Ashley Uzer

Ashley Uzer is a freelance writer who specializes in sex and dating. She has written for many international outlets including Bustle, VICE, & Galore. She’s currently doing the whole digital nomad thing, but you can find her in Washington D.C. or NYC every once in a while. Follow along with her adventures on TwitterInstagram, or on her blog.

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