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Date Night Outfits: Casual to Romantic

It seems like the only way to start a post about what to wear on a date is with a congratulations: Congratulations! You’re going on a date!  Whether it’s a first date or a casual go-out with a longtime significant other, spending time with someone you might like or do like—or love!—is something to be grateful for.

But date night outfits are one of those illusive fashion categories that, no matter how many dates you’ve been on, can still be tough to nail down. Why? Because, honestly, the possibilities are endless, and when romance is involved, things can get complicated!

There are, however, some tried and true guideposts for finding the right date night outfits, and THAT’S what this post is all about. Let’s dive in, lovebirds.


Before you even dip into your wardrobe and try to put together an outfit, do a little research! A couple things—

First, where are you going on your date? Hop online and check out whatever location you and your date have planned, and measure the formality, the edginess, the general vibe. You’ll want to be in tune with the atmosphere, so take a quick survey and see what clues you can find that might point you in the right direction.

Secondly: check the weather. Take a peek at what the sky might be doing the day of your date. Whether it’s dry or rainy, hot or cold will obviously influence which date night outfits you choose.

After you have a good idea of what the weather and location may call for during your date, the next and biggest thing to keep in mind is this: the most important thing when determining what to wear on a first date or any date is comfortability. If you are not comfortable in your skin and in your outfit on your date, it’s going to show.

So, if you put together an outfit that fits the weather and location, but you still don’t feel comfortable, you should probably try something else. Most dating coaches will tell you that your energy going into the date will largely determine its outcome—so if you’re feeling off about what you’re wearing, it’s not going to do you any favors.

Make sense? Now let’s look at some specifics.


The first thing to remember when deciding what to wear on a first date is this: be you. It sounds simple, but it is absolutely paramount that you feel comfortable and relaxed in your outfit. That you feel like you. That’s a bit of a reiteration of what we said above, but it’s that important!

OK, let’s look at a few different first date scenarios to form a framework for how to approach what to wear on a first date.


A very popular option for that first date is a semi-swanky romantic dinner. He wants to wow you with his great taste in wine and ability to pick up a big tab, so let him. But what to wear?

It doesn’t get much better than a little black dress for a classy date night outfit. Black dresses come in all shapes and silhouettes, so study up on the location and maybe use atmospheric clues to choose one. Imagine the candlelight flickering over your shoulders in this ruched mini! Knockout.

If the vibe isn’t quite candlelight, it’s an opportunity for denim-lovers to stay easily within their comfort zone and put together some great classy date night outfits. Trade typical blue jeans for a dark wash or black skinnies, and you can easily create a chic look that’s formal, but not dress formal. Try a pair with a flirty blouse to capture your date’s attention.


Hitting the cinema is also a big pick for first dates. A little typical? Sure, but that doesn’t mean you have to look typical. The main thing to think about when deciding what to wear on a movie date is comfort—you’re going to be sitting in a theatre for a couple hours, so plan accordingly.

You’ll certainly want to wear a longline sweater or comfy cardigan, as movie theaters tend to be pretty chilly. A good sweater (like this mesh knit cardigan) can keep you warm and comfy without throwing your style game off: When it comes to bottoms, a pair of tight jeans might end up feeling constrictive in a theater. You’re better off with some wider-leg pants in a different fabric than denim. Try a sexy wide-leg with a simple top and your sweater to nail cinema chic.

If you really want to wear a dress, that’s fine for movie dates as well. You’re just going to want to choose something that allows for greater mobility. A bodycon mini probably isn’t the best selection for a film date. Try something with more breathing room and a fabric that’s more geared toward comfort.

(Oh, and side note: maybe throw some breath mints in your bag/purse/clutch. They might come in handy. Just saying.)


Sometimes dates are as casual as just hitting a great bar. A good rule of thumb when dressing for casual dates is staying on the higher end of the style spectrum.

Sure, it might be appropriate to wear blue jeans and a T-shirt, but will that wow your date mate? You could elevate your game with a lowkey mini or midi dress to stand out while you’re shooting pool. Try a T-shirt dress or another comfy option with a moto jacket for a killer bar look.

Casual dates like happy hour dates also tend to turn into more time on your feet, and can often wind up becoming an impromptu barhop. When choosing some date night heels, go for a wider heel, and maybe a mid-height to maintain maximum walkability.

This isn’t to say denim is off the table for happy hour dates. No way! If you want to stick with a nice pair of jeans, a simple basic on top and a flourished throw or sweater, you’ll still be slaying it. Maybe show just a *little* skin on your legs with some bold distressed denim.



We hope this has given you a good start for putting together the date night outfit that makes you feel like YOU and still stuns, whatever the location and level of formality. Remember—just relax and have fun with it!

Use these style tips as guideposts, and he’ll never regret swiping right.


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