Don’t Sweat It: What to Wear on Every Possible Summer Date

Whether it’s your first or 100th, date nights always come with a little bit of added pressure compared to an ordinary day. Excitement, nerves, a little bit of overthinking—you’ll probably experience the full spectrum of human emotion before you even leave the house, which means the last thing you should be stressing about is your date-night outfit.


Just like the date itself, date-night outfits should be a little special. After all, you want to look and feel your absolute best, which means that you don’t want to be messing with an ill-fitting top or worrying about anything other than the person you’re with. Add in the layer of summer heat (and inevitably sweat) working against you, and you have a little bit of thinking to do—or you would if we didn’t do it for you.

Whether you’re headed to a patio for dinner for a glass (or five) of wine or going on a romantic picnic, we’ve figured out the perfect thing to wear, so what you remember is the date itself—not your sweaty thighs sticking to the back of your chair or running to the bathroom to dry your pit stains under the hand dryer. 


To a rooftop bar

Is there a joy as great as a rooftop bar in the summer? We say not. There is nothing as put-together and fuss-free as a midi dress, and in a fun, summery hue with dressed-up accessories, you’ll feel like the 10 you are, no matter where the night takes you. 

To a baseball game

Whether you’re there to watch baseball or simply to sip on a foot-tall margarita and eat a hot dog, you’ll feel cute doing it in this, and that’s a win for you—regardless of what team wins.

On a picnic

A picnic date sounds like a romcom-worthy dream come true, but when you’re going on one, in reality, it poses an important question: What in the hell do you wear for a date where you’re sitting on the ground? The answer is linen pants. You’ll be comfortable sitting down (and won’t have to worry about a dress blowing up or accidentally flashing anything you’d rather them not see yet). Make it a monochrome moment with a top in a similar hue, and you’ll feel the perfect level of dressy.

To a patio dinner

In glorious summertime, we’re simply turning to dresses as much as we can—especially for a nice dinner out. For an extra dressy feel, opt for black and top it off with heeled sandals and summery accessories. It’ll hit the perfect combination of being seasonally appropriate and also being fancy enough for that reservation you’ve been waiting months to snag.

To an outdoor concert

An outdoor concert look should prioritize fun over anything else, and what’s more fun than a pair of patterned pants? We rest our case. Opt for sneakers so you can stand and dance all night with ease and a tank top so that armpit sweat is no match for you. Finish it off with a statement bag, and you’ll be the best dressed one there.


On a walk to get ice cream

For a casual walk to grab ice cream at a local spot (preferably two scoops of superman ice cream or Jamaican grape nut), an easy, breezy romper and flat, walkable sandals are your best bet. Finish it off with a hydrating lip stain, won’t budge all night, and will provide an extra summery pop of color.


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