16 Cute & Casual First-Date Outfits For Any Kind of Date

by Alexa

With Valentine’s Day approaching, I wanted to share with you some first-date outfit ideas. Even though these are “first-date outfits,” you can wear them while taking yourself or your friends out on a date too!

I’ll show you everything from casual to fancy outfits to get you in the spirit of love. Pretty much everything I'm wearing here was thrifted, so you can see how to easily create fun Valentine's outfits out of thrifted items.

What to wear on a Zoom date

1. Zoom date

This outfit is perfect for Zoom dates when you can’t meet in person. For this outfit, we’re going simple but with a few added details.

Pair a satin silk cami with a biker jacket to add a bit of edge, then throw on some accessories, like a gold choker necklace. It’s simple but all the details make for a unique look.

What to wear on a picnic date

2. Picnic date

When thinking about picnic dates, most think of cottagecore and short dresses, but be practical. If I’m sitting on the ground, I’m wearing shorts!

This 'fit is super dreamy and cute. The pastel works well with nature around you. 

Casual first date outfit for a cafe

3. Coffee date

My favorite date is definitely a coffee date because you’re not stuck and you can leave at any moment.

This is a very hipster look for when you’re feeling it out and seeing what the person is like. Go for neutrals to keep it safe.

Cute first date outfits

4. Lunch date

The lunch date is another pressure-free date, so I've opted for fun pastels again.

Wear something you like that other people might not. Everyone says you should dress for your date, but dressing for you helps feel out if someone is or isn’t for you. I’m wearing a puffy headband that a lot of people hate but I love!

First date outfit ideas

5. Library date

This outfit should be comfy and artsy, and of course, I’m wearing my glasses if I’m going to read. I tucked in the front of the sweatshirt for a more modest, chill look - a perfect casual first date outfit.

How to plan a first date outfit

6. Thrift date

As someone who loves thrifting, this is the outfit I would wear to a first-date thrift date!

Showing one shoulder keeps it playful and this date provides the opportunity to show off your style while gauging theirs. 

Sexy first date outfit

7. Dinner date (when you already know them)

This outfit is for dinner dates when you already know the person, but it’s your first time in a romantic setting.

Wearing a corset with a leather blazer over the top, you get to decide when to play modest or show skin. This outfit is so sexy, and with the knee-high boots, you’ll feel powerful.

First date dinner outfit

8. Dinner date (when you don’t know them)

I wanted to remain covered up but still stand out, so I chose a gold, silky button-up. This is a great example of picking different materials to ramp up the style of an otherwise plain outfit.

First date outfit for a night on the town

9. Night on the town date

This is a city look for those “being together and seeing what happens” dates. This outfit is pretty safe, but the turtleneck feels and looks sexy.

Don’t forget the comfy shoes if you’re going to walk a lot! Add a blazer if the weather is cool.

What to wear to an outside date

10. Outside walk date

This is my outside-walk date look. By outside, I mean all flat surfaces and no hikes! This dress is so beautiful and simple, and I added a puffy sleeve blouse to tie it together. 

What to wear for a drive-thru date

11. Dinner in the car date

If you’re anything like me and you’re eating food in the car, you’re definitely going to spill something, so it’s best to wear all black.

Opt for a nice sheer black long-sleeve shirt and put your hair up so it won’t fall in your face while eating.

What to wear to a first date at the movies

12. Movie date

If you’re going on a movie date, you’re probably unsure about the person. I went with this silky-satin top that’s dressy but toned down and paired it with a casual jean jacket.

What to wear on a dinner and a movie date

13. Dinner and a movie date

Dinner and a movie is the classic first date. Wear a jean jacket, but this time with a super dressy satin-silk dress. The jean jacket and the shoes tone down this look so it works for both settings.

What to wear on a date to a cat cafe

14. Cat cafe date

Starting a relationship off with cats always works! This outfit is super casual, but the shirt is sleeveless, so you can throw a lacy bra under it for a sexy edge.

What to wear on a concert date

15. Concert date

Concert dates are some of my favorites. They’re a great way to see someone’s music taste, or if they can get into things you like.

The black works great for concerts because you’re going to get sweaty and the pants show a lot of personality.

What to wear on a flea market date

16. Flea market date

Ending on a casual note, this outfit is great for casual shopping dates. Wear a slogan tee that’s relevant to you and throw a cardigan over it for a casual, this-is-me kind of outfit to show off your personality.

First-date outfits tutorial

That’s all the first-date outfits I have. You’re now equipped to go out on your first, second, and third dates!

Let me know which of these outfits is your favorite in the comments below and where you would go on the perfect first date.

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