9 Non-Dated Ways to Wear Shorts This Summer

No matter where you live in this vast country of ours, at one point or another, you’re probably going to want to wear shorts during the summer. But as far as summer staples go, shorts aren’t exactly the most fail-safe item to style. There are many different types of shorts, and figuring out what to wear with them can take a bit of trial and error. 

Shorts trends don’t change all that often (just consider how long bike shorts and cut-off denim shorts have been a thing), so coming up with fresh ways to wear them is of the utmost importance as the weather warms up. Since spring is in full swing and shorts are coming back into our outfit rotation (I don’t know about you, but it’s going to be 90 degrees this week where I live), now is the perfect time to think about how to put together shorts outfits that aren’t just the same old thing. To avoid looks that seem a bit dated, I found nine new ideas for you, as worn by some of Instagram’s most stylish. Keep scrolling to find out how to try them for yourself and shop similar shorts to wear on repeat. 

Pair khaki shorts with a tank and sweater draped over your shoulders. Complete the look with classic sneakers.

Make boxer shorts street-appropriate by pairing them with a tank and oversized third piece.

Make your long denim shorts feel even fresher by pairing them with other trends—in this case, a sweater vest and clogs.

The chicest way to wear white shorts is with other white pieces. (Just be sure to avoid the espresso and red wine.)

Long, fitted denim shorts are best worn with heels (trust me). And something simple and polished like Lucy’s cardigan will never look dated.

Chloe’s barely there heels and barely buttoned cardigan make her casual shorts undeniably chic.

A blazer makes everything better, and the Converse sneakers make everything cooler.

Bike shorts aren’t just for workouts, as evidenced by this outfit. All you need is an oversized white button-down and New Balance (or any other) sneakers.

Don’t overthink sweatshorts—just add an oversized T-shirt, crew socks, and sneakers and you’re out the door.

Peachy plissé pleats for the win.

Just in case you’re tired of denim cut-offs.

I ordered these myself and can confirm the fit is excellent.

Madewell shorts never let me down.

I’m tempted to just order these in every color.

A classic option.

Donni sweatshorts are 100% worth it.

I highly recommend adding these to your Amazon cart.

These are a Who What Wear editor favorite.

Next up, here’s how to recreate Hailey Bieber’s controversial shorts outfit.