6 A+ Ways the Fashion Crowd Are Styling Their Shorts

Growing up in sunny L.A., shorts were a mainstay in my wardrobe. Denim shorts, linen shorts, drawstring track shorts, my beloved Soffes—I'd wager shorts made up about 50% of my dresser drawers. But somewhere between getting older (where I spend most of my time in more formal settings) and moving to the East Coast (which sees significantly fewer warm-weather days), my shorts count has whittled down to a few fraying pairs of denim cutoffs. While they're useful for beach getaways, my 10-year-old jean shorts feel too informal to make a proper outfit from. 

Enter my obsession with saving every stylish shorts ensemble I come across on Instagram. The fashion crowd has been taking to the silhouette more and more over the last few months. With the right styling and the right cut, shorts are proving to be an aspirational option. It helps that brands have been releasing chic iterations like leather culottes, cool linen Bermuda shorts, knee-length denim cutoffs, designer bike shorts. Ahead, these ladies show us six cool ways they style their shorts that'll have us reincorporating the style into our wardrobes at some point this season.

Dressy Bermuda Shorts + Slim-Fit Blazer

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(Image credit: @alyssainthecity)

If you would have told me three years ago that Bermuda shorts would become one of the coolest trends, I wouldn't have believed you. But with chic trouser-esque versions like this, I'm happy to be proven wrong. Channel Alyssa Coscarelli's half boardroom, half equestrian star ensemble by pairing your knee-length trouser shorts with a fitted blazer and a tall pair of boots that just meet the hem of the shorts.

Cargo Shorts + Knee-High Boots

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(Image credit: @annasarlvit)

I am always on board for an almost monochrome outfit. By almost I mean one that sticks to the same color without being matchy-matchy. Case in point, Anna Sarlvit's cream-and–light yellow getup. I will forever be attempting to make a pair of cargo shorts, a long leather coat, and lug-sole boots look half this good.

Denim Bermuda Shorts + Printed Sweater

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(Image credit: @ada_oguntodu)

If you're a jean-cutoffs devotee, denim Bermuda shorts are an easy way to step it up without sacrificing your personal style. Ada Oguntodu proves even frayed-hem denim shorts can be dressed up with a few unexpected touches like a doodle-print sweater and bright-white pumps. 

Drawstring Running Shorts + Oversize Blazer

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(Image credit: @emilisindlev)

Emili Sindlev's outfit proves there's still so much creativity in fashion that has yet to be explored. Turn your high school track look, basic white tee included, into a bona fide street style outfit with a large-fit blazer and a bold set of mules. 

Wide-Leg Shorts + Mid-Calf Boots

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(Image credit: @micaelaverrelien)

If you walk away with one thing after reading this article, let it be that a blazer is the sole trick you need when it comes to dressing up your shorts. The balance of the wide-leg shorts with the fitted blazer creates a cool A-line silhouette. Since a pair of linen shorts can look quite causal, use the help of some mid-calf boots to give the outfit a more put-together feel. 

Leather Culotte Shorts + Platform Sandals

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(Image credit: @greceghanem)

If you're looking for the pair of shorts just about every influencer is adding to their spring and summer wardrobes this year, you've found it. These Frankie Shop faux-leather culottes have become omnipresent and for good reason. They're easy to style—they pair well with just about any top or sweater—and the leather-look material makes them look more formal than any other kind of shorts. Feel free to wear the shorts with heels, strappy sandals (as Grece does here), or even sneakers. 

Up next, how to tackle spring suiting for as little as $50 a piece.

Contributing Editor

Ray Lowe is a contributing editor for Who What Wear. She's spent the last decade living in New York, but now that she professionally works from home, she's slowly been going back to her roots by splitting time between NYC and L.A. A year ago, she left a four-year stint as a fashion editor for Refinery29 to explore the freelance life. Nowadays, she does just about everything from penning online articles (for Who What Wear, Refinery29, Elle, Cosmo, and many more) to writing scripts, styling, and finding ways to fuse her love for both Disney and fashion. Her main beat is fashion (trends, emerging brands, affordable finds, you name it), but you may find her dropping in with a beauty story every now and then. As for her personal style, she'd best describe it as a balanced blend of basics and contemporary trends, often with a dash of Mickey Mouse thrown in for good measure. In her spare time, she can be found coddling my pets (a French bulldog and a rescue cat), curating travel itineraries for her friends, scrolling through Instagram for up-and-coming brands, and watching so-bad-they're-good films.