What to Wear on a First Date: 10 Cute And Casual Outfit Ideas

So, you’re wondering what to wear on a casual first date? Choosing the perfect first date outfit can feel like a right dilemma. On one hand, you want to look cute and make the best possible first impression. On the other hand, you don’t want to look like you’re trying too hard or feel like you’re overdressed for whatever first date activity you’ve planned. Don’t stress—I’ve got you covered with 10 casual first date outfits for meeting up with that hottie from Hinge.

Before I jump into the first date casual outfit inspo, let’s look at some of the most important things to consider when you’re choosing what to wear on a first date.

Related: 15 Dating Experts on What to Talk About on a First Date

What to wear on a first date

Firstly, you want to make sure your outfit is appropriate for the weather. This should go without saying, but a first date is one time you don’t want to be too hot or too cold in the name of fashion. If you dress too warmly, you run the risk of being a hot, sweaty mess on your date, which might knock your confidence. If you dress for a hot day and it’s cold outside, you’ll be shivery and shaky, which also isn’t a great look.

The most important thing when you’re deciding on your first date outfit is that you feel comfortable. If you’re uncomfortable in your outfit, it’ll only add to your first date nerves and serve as an unneeded distraction from enjoying the person you’re with.

You also need to ensure your first date outfit is suitable for the activity you’ve chosen to do. Dinner and drinks dates are easy to dress for, but active dates like bowling or rock climbing add a few constraints.

Finally, remember to pick an outfit that highlights your regular style and personality. If you’re someone who dresses in pink, a first date isn’t the time to start dressing in all-black just because you think it’ll impress your date. Yes, put your best foot forward, but remember that dating is all about figuring out whether you’re a good match for each other—not about trying to fit into some ideal that you think they will like.

Related: 21 First Date Tips To Boost Your Chances of Getting a Second Date

10 Casual First Date Outfit Ideas

Outfit #1: A blue maxi dress and cute flats

Casual First Date Outfit
Credit: @oliviarose on Instagram

This is the ideal spring or summer first date outfit, as you’ll look effortlessly chic without overheating—and we all know just how stressful a sweaty first date can be. It’s versatile and can be worn on most kinds of first-date activities, such as a picnic, drinks, or dinner. But maybe skip this one if you’re planning to go rock climbing! Opt for a high-neck maxi dress if you prefer to dress more conservatively for a first date, or pick a backless style to add some subtle sexiness to the look.

Shop the look: 


Outfit #2: High-waisted boyfriend jeans and a cropped shirt

Credit: @lauravanessa_w on Instagram

When it comes to looking good on a first date, the first step is feeling good. If you feel comfortable in your first date outfit of choice, you’re more likely to come across as someone who is comfortable in their own skin. And what better way to feel comfortable on a date than turning up to a first date in a pair of (cute) boyfriend jeans. Pair with a cropped shirt (low cut, if you dare) and either cute sandals or sneakers depending on, again, what makes you feel most comfortable.

Related: Had a Great First Date? Here are 9 Tips for the Second Date

Shop the look:


Outfit #3: White on white

Credit: @portrayingmystyle_ on Instagram

While wearing white on a first date does increase your chances of a wardrobe malfunction and precludes you from drinking red wine if you’re anywhere near as clumsy as I am, an all-white outfit looks undeniably sophisticated and laidback. This outfit scores bonus points from me because I can eat as much as I like without the waistband digging into my belly. If you’re accident-prone, consider swapping this all-white look for a darker shade.

Shop the look:


Outfit #4: Dress down a short skirt with sneakers

Credit: @amandinebru__ on Instagram

I’m all for wearing sneakers on a first date. They’re comfy (tick), they’re practical (tick), and there’s less of a chance that you’ll stack it and embarrass yourself in front of a stranger you met on a dating app (tick). They also can take a dressy outfit—like this cute skirt and top—and turn it into the perfect casual outfit for a first date. This outfit is equally suitable for a daytime activity, like a picnic or coffee, and an evening date like drinks or dinner. Dress it down even further by swapping the top for a simple white tee.

Shop the look:


Outfit #5: Floral dress with sneakers

Credit: @julesfi on Instagram

A gorgeous floral dress can make the girly side of your personality shine through on your date. Paired with some classic white Converse, this look is dressed down without being too casual—because you never know: Maybe you’ll hit it off and your casual daytime date could turn into drinks and dinner. I particularly love how this dress from Reformation has a thigh-high slit, turning a cute floral dress into something a tad sexier.

Related: An Argument For Letting Your Inner Freak Flag Fly On The First Date

Shop the look:


Outfit #6: Jeans, a white top, and a blazer

Credit: @amyrowleyy on Instagram

Are jeans too casual for a first date? No freaking way. A great look for when you’re headed on a date straight after casual Friday at the office, this outfit takes a simple jeans and t-shirt combo to the next level with some small details: A blazer, a cute belt, and a great pair of shoes. Swap the shoes for a pair of classic white sneakers to create an even more casual first date outfit, and spice up the look by swapping the black blazer for something in a brighter hue—pink, perhaps?

Shop the look:


Outfit #7: A midi-length shirt dress and sneakers

Credit: @cocobeautea on Instagram

Shirt dresses aren’t just for the office, they also make a really cute outfit option for a first date. Paired with sneakers, slides or low ankle boots, and a belt to accentuate your curves, a shirt dress can—believe it or not—look sexy, cute and sophisticated at the same time.

Shop the look:


Outfit #8: Midi skirt and a crop top

Credit: @theishitaedition on Instagram

I love this outfit—it’s super classy and the hint of skin adds a little sexiness to what is otherwise quite a conservative first date outfit. This look is super versatile and can be worn for daytime and nighttime dates alike. In winter, simply throw a long coat over the top—or swap the cropped shirt for a cropped sweater instead—and opt for ankle boots or sneakers instead of summery sandals.

Shop the look:


Outfit #9: Bright pants and a cropped tee

Credit: @djamilastanic on Instagram

If you’re the kind of person who loves to wear bright colours and bold prints, there’s no reason why you should mute your style simply because you’re going on a first date. I love this look because it’s loud and fun, while still being an appropriate outfit for a casual first date. Keep the accessories simple and allow your bright pants to make a statement. Bonus—you can tell your date “I’m the one wearing bright pink pants” and avoid the awkward, “excuse me, are you Kate?” exchange.

Shop the look:


Outfit #10: All in black

Credit: @thanyaw on Instagram

If bright colours and crazy patterns aren’t your thing, that’s okay. There’s nothing wrong with wearing all black on a first date—though I would suggest adding texture or pattern like the one above to add some personality to your outfit. As for the ankle boots, opt for flat or heeled boots. Now, you might be thinking, should you wear heels on the first date? It depends—do you feel comfortable in them? Are they suitable for the activity you and your date have planned? If your date has planned a surprise, you run the risk of turning up to laser tag (or some other equally inappropriate situation) in stilettos… Not ideal.

Shop the look:


Now, go forth and slay this date. You’ve got this!


© 2022 SheSaid. All Rights Reserved.

Scroll To Top