How to Wear Shorts

• Part of our How to Wear It series •

How to Wear Shorts Like the Summertime Goddess You Are

by Madeline Berger
April 21, 2021

After a winter that felt simultaneously two and twelve months long, it’s finally April and spring has officially sprung. Dear reader, what is synonymous with the arrival of these warm months? Patio drinks, driving with the windows down, and cute summer clothes we can start throwing on when the temps pass 50. We’re here today to celebrate this much-needed thaw and delve into the world of how to wear shorts.

Maybe you love shorts. Maybe you’re even that person who’s been spotted wearing them while gassing up your car in January (please stop). Or! Maybe you’ve been wondering how to feel cool and comfortable in shorts since approximately 9th grade. I’m here to tell you that the possibilities are truly endless when it comes to wearing shorts and present you with a bounty (read: sixteen) of fashionable folk who truly know how to rock a pair of cutoffs. From knee-grazing Bermuda style shorts to classic denim cutoffs to of-the-moment sweatshorts (you read that right), scroll on for some serious inspo on how to wear shorts.

Credit: @jessylaw

Have a pair of good ol’ athletic shorts you just can’t bare the thought of changing out of? Throw on a coordinating tube top and oversized jacket for an instant twist.  

Credit: @samue1oh

Add interest to a pair of classic denim cutoffs but layering t-shirts, adding accessories like a belt and sunglasses, and throwing on tall crew socks to play with proportions.

Credit: @casakaterina

Bermuda-length chino shorts are given an instant lift when paired with a blouse, loafers, and a large-brimmed hat. We love Katerina’s earth-toned color combo!

Credit: @juliaadang

Loving early aughts fashion lately? Take a note from Julia and throw on a pair of cargo shorts with a pastel-hued sweater for a soft yet utilitarian look that’s an A+ for 2021.

Credit: @dualipa

Dua Lipa got a trending shorts look down perfectly by pairing sweat shorts with a shrunken cardigan, chunky, colorful jewelry and a bandana in the hair.

Credit: @griztriz

Play with those classic three-stripe Adidas shorts by pairing a striped shirt in a contrasting color. Don’t forget the bucket hat and sick sneakers!

Credit: @tamarabellis

Instantly elevate a pair of denim shorts by pairing them with a romantic, flowy top perfect for that summer heat. Add heels and clutch for a perfect Date Nite Look™.

Credit: @ooutfitzz

A hastily tied shoestring belt gives denim shorts that coveted, skater kid look. Layer tops of different lengths and throw on a baseball cap for a very Californian outfit.

Credit: @vintageshadeson

Vintage floral shorts are trending hard this summer and go perfectly with a flowy top and trainers. Tie your blouse at the waist and throw on statement earrings for a perfect summertime look.

Credit: @annaaborisovna

White shorts look instantly fancy when worn with a sheer top in a monochromatic hue. We love how Anna played with proportion by wearing an open dress and adding contrast with a chunky belt and oversized sunnies

Credit: @seanaveli

Sometimes, you just don’t wanna mess with a good thing. Pair cargo shirts with a graphic tee, sneakers, and a baseball cap for an instant outfit that’s ready for boppin’ around town.

Credit: @thesensiblefay

We love a men’s jean short on anyone and everyone, especially when given a twist like being worn with a lingerie-inspired cami and platform boots. Throw on a denim jacket for Canadian tuxedo magic.

Credit: @ashbegash

Perfect for those cooler summer evenings, denim shorts are great when worn with a simple sweater. Give it a little tuck in the front and throw on sneakers for a quick, cute look.

Credit: @drewallenharrison

Bring out your inner prep by pairing structured white shorts with a tucked-in t-shirt, white trainers, and a matching baseball hat. Hit the tennis courts or the nearest patio!

Credit: @143nhi

Maximalism is the new minimalism, especially after a year of sweatpants. We love long shorts paired with knee-high socks and a bikini top: It totally plays with proportion and results in an unexpected outfit that’s all kinds of fun.

Credit: @alyssainthecity

Alyssa takes on texture by pairing berry-hued corduroy shorts with a flowing crop top. A handbag in a complementary color makes this a simple yet perfect look for a meal on the patio or stroll through the park.

Ready to shop for your own perfect pair of vintage shorts? We’ve got styles featuring everything from classic denim cutoffs to cargo shorts. Our small team hand-selects every item in our vintage shop and new items are added weekly. Click below!