What To Wear On A First Date

What To Wear On A First Date

As someone who is in their early 30s and still single, I’ve been on a lot of first dates! I actually don’t HATE them either. It’s fun to get to know someone without really any expectations. In this current dating culture, first dates are usually fairly quick. A drink, a coffee, nothing crazy. But regardless of how you met, a first date is still a bit stressful. You definitely want to dress the part and give off a good first impression. All while feeling your best and most confident in the right outfit.

What To Wear On A First Date

You definitely want to gauge your first date based on the vibe of the location you pick. Is it more casual? Will you be outside going for a walk? Or is it more dressy like a nice hotel lobby bar? There are so many different types of first dates to consider your outfit of choice. Here are a few ideas!

Post Work Happy Hour Date

An easy, casual date that requires little effort in terms of your outfit. If you both agree that it’s a post-work happy hour date, you can definitely show up in your work clothes and not be too worried about looking anything but office appropriate. If you like, you can swap your blazer for a fun leather jacket, or bring a more sexy heel. So long as you BOTH know it’s a post 9-5 date, don’t stress too much here. Below are a few favorite looks that work for the office and would be great to crossover to a first date too.

a woman in a worWhat To Wear On A First Datek outfit
What To Wear On A First Date
What To Wear On A First Date
get the look

Cocktail Date

A cocktail date, whether it’s during the week or the weekend, can still be a bit casual. But definitely step it up a bit! I personally prefer this kind of date over anything else. You can commit to one drink and go for a second if things are going well. And for me, I like to get there early so I can have a little pre-drink to get rid of any first date jitters. But one drink allows you to also have an out. Once you’re done, so is the date.

I like to keep things casual but slightly elevated. My got to are always jeans. But wear your favorite kind of bottom that makes you feel good. I usually wear jeans and a nicer top. Just add a bootie or simple heel. For fall and winter, I like to throw on a great jacket like a suede moto one, leather or a fashionable blazer. If you’re a dress person, this is a great option too, but not required if it’s not your thing.

A flirty look in a mustard top and plaid blazer
white wrap dress, little white dresses for spring - My Style Vita
blue suede jacket, jeans for date night
get the look

Coffee Date

You either like or dislike a coffee date. I’m not a big fan since I enjoy a little liquid courage on first dates. But if you’re grabbing coffee you can definitely be more casual. Fun sneakers or booties, jeans and a graphic tee with a jacket are perfect. I also love a good chunky sweater and high waisted jeans with booties. For the summer, choose a flowy summer dress and a sandal. A denim skirt and sandals with a tank is also great. Simple, casual but still put together. I feel like a coffee date is just my cocktail date outfit but more casual. Swap heels for sneakers or booties, add a denim jacket to the dress, and so on. Here are a few outfit ideas!

for the fall
Jessica Wearing Everlane Denim
date outfit ideas
date outfit ideas
get the look
for the spring and summer
Jessica dresses to impress in a t-shirt dress
date outfit ideas
date outfit ideas
get the look

Movie Date

Movies are super casual and I like to be comfortable! Those reclining chairs are the best, right? For any movie date, I always go comfortable in jeans, tee, and sneakers. You can swap sneakers for booties, loafers or any flat you prefer. Bring a sweater or cardigan as movie theatres tend to get cold. I’m a big fan of a third piece to pull an outfit together no matter how casual it is. And cardigans, sweaters, or light jackets do that perfectly!

Fancy Dinner

I’ll be honest, if someone asked me to dinner on a first date who I hadn’t met before, I would say hard no. BUT, if you know this person, or you met previously and that’s how the first date came about, go for it. A fancy dinner date night is always fun anyway, right? For a nicer dinner, choose a pretty cocktail dress, or nicer dark jeans with a silky blouse, blazer, and stiletto. It’s a timeless look in my book.

fancy dinner outfit
fancy dinner outfit
fancy dinner outfit
get the look

How To Choose Your First Date Outfit

When planning your first date outfit, there’s definitely a few things to consider. The weather, the activity, and what makes you look and feel good. Here are a few things to keep in mind before you head out the door for your next date!

Consider The Weather and Location, Indoor or Outdoors?

Are you planning to sit on a patio and have a margarita? Or go for a walk? Or will you be posting up at your favorite restaurant’s swanky bar? All of these things play into what you choose to wear on a first date. You definitely still want to feel good and leave a great first impression. So keep in mind these things. If you’ll be outside in the heat, maybe opt for a flowy cotton dress so you can handle the sweat! If it’ll be indoors at a restaurant, you may want to bring along a light jacket.

Think About The Activity

I love a good activity date. Whether it’s going bowling, or just a walk in a fun part of town, or playing darts at the bar, think about what you’ll be doing and if you’ll need to choose comfortable clothes.

I’ll never forget going on a date with a guy I was seeing and was totally thrown off. He wanted it to be a surprise and I had no idea what it was we were doing. I even ASKED what I should wear and he said something nice but nothing crazy. Men, they don’t understand how to explain these things I suppose. I went with a casual but nicer mini dress and some high heels. Nice, but not too nice! Still a touch casual, but showed just enough skin for a fun date. It ended up being a casual cooking class and I basically looked like an escort. It was embarrassing. Everyone else was in jeans and sneakers ready to get their hands dirty and cook! I dumped him that night.

Anyway, moral of the story, know the attire expectation when planning out your date outfit so you don’t feel like a fool!

And Don’t Forget, Show Just Enough Skin

If showing a little skin isn’t your thing, that’s fine. But if it is, go for it! It can make you feel sexy, confident and why not show off parts of your body that you’re proud of! Have you been killing it in the gym to get those Michelle Obama arms? Show them off, girl! Or do you have great long legs, throw on a mini skirt. There’s no harm in this if it makes you feel confident and comfortable in your skin.

Photos by Hannah Lozano

Jessica is an Atlanta life and style blogger. Aiming to bring practical tips to your every day life. Tips that you can easily tackle and make your life feel just a tad more 'put-together'.

Leave a Comment


  1. 1.13.20

    So many great looks for date-night! Love the spring and summer looks most!

    Cathy, your Poor Little It Girl

    • 1.14.20
      Jessica said:

      Same! Best time for dates too, no one wants to get a drink at 6 pm when its already dark out ha!

  2. 1.14.20
    Radi said:

    This is so cute. Love the whole post and your outfits. Now I just need to find a date to go to LOL!