How to Pick the Perfect First Date Outfit: The Definitive Guide for Women 2023

Updated: February 3, 2023

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.

1. Throw all the first date outfit advice you’ve ever heard out the window

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.

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

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.

3. Wear something that makes you feel good

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!

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

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!


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