What To Wear On A First Date In Summer: 5 Different Outfits for 5 Different Dates

First thing’s first, it depends on who and how you are.
What I wear on a first date could be totally different from you.

What to wear on a first date in summer

To figure out what to wear on a first date in the summer (or any season, really), you need to figure out what you want your clothes to represent and what you want to present.

What do you want the other person to know about you?

When I get dressed for a first date, I start there.

Actually, that’s a massive lie. I don’t even think about it anymore because I have a first date outfit that I re-use over and over… It’s also the “my crush will be at this BBQ” or the “my ex-crush will be at this BBQ” outfit. It’s a multi-functional outfit that I wear whenever I need to feel perfectly me.


When I wear my Kate Moss Topshop sundress, I know I’m going to be the best version of myself. It makes me feel open and like myself.

Like Bill Cunningham said…

Your clothes protect you.

I struggle with letting my guard down and opening up. I don’t want to run the risk of being stand off-ish or cooler than thou on a first date. If I wear a too-cool outfit, I know I’ll be a bad closed-off version of myself.

So on a first date, I wear clothes that lower my guard and make me feel more me, i.e. sweet summer sundresses.

When YOU get dressed for a first date, you need to think about that…

What do you want to convey and portray?

After you answer that first question you can go a little more practical…

1- What time is the date?

2- Where are you going?

3- What’s the weather going to be like?

Let’s run through some types of first summer dates and what to wear… other than that Kate Moss Topshop dress.

Coffee Date Outfit

In my opinion, coffee dates mean that the person is interested in getting to know you, but doesn’t want to come off too strong by asking you out for drinks.

It’s not as serious as committing to eating a full meal with a person…. and since it’s pretty casual, a coffee date is when you can wear your most relaxed outfit.

A simple black cami with patent flats makes the outfit a little more pulled together.

What to wear on a first date coffee

Lunch Date Outfit

Even though “it’s just lunch” (I actually typed that out then realised that’s actually a dating service that I read an infomercial for in Alaska Air’s in-flight magazine (yes, I read in-flight magazines)), you’re still sharing a meal with someone.

So, look for an outfit that’s sunny, but relaxed. This cherry printed HVN dress is perfect for that… Also, try to grab a table outside, everyone is happier when the sun is shining on them!

What to wear on a first date lunch

Dive Bar Drinks/Casual Date Outfit

A date that takes place at a dive bar, wine bar, or any bar is pretty casual.

… which is good because that means any outfit can work.

Personally, I’d go for an outfit that balances nice and messy.

What to wear on a casual first date in summer

Dinner Date Outfit

Someone who asks you out for dinner is probably somewhat serious — like unless something goes horribly wrong, both of you are committing to spending at least an appetizer together (but hopefully more if you like them!).

Unless you’re going to In-N-Out (mmm…), dress a little dressier, but still a little bit casual and approachable.

Réalisation Par’s Ozzie’s star print is great for a casual dinner. It’s a little dressy, but the tan suede bag offsets it.

What to wear on a first dinner date in summer

Fancier Dinner Outfit

Go for something that’s somewhat demure, but still a little flirty.

This Isabel Marant skirt and top combo (bought on the Real Real) is sweet, but sophisticated.

What to wear on a fancy first dinner date in summer

These outfits are just suggestions, of course. What YOU wear on a first date in the summer really depends on just that, YOU.

Forget about those articles that say men subconsciously love women in red and only expose your elbows if it’s a Tuesday.

If you feel comfortable & confident and if your outfit makes you feel and act like the best version of yourself, go for it.

A first date should make you feel happy…. and your outfit only adds to it.


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