21 New Ways to Wear Shorts This Season

Before you know it, it’ll be shorts season — both inside and outside. And while we’ve all got a trusty supply of Bermudas, cutoffs and everything in between, we don’t have a Rolodex listing lots of ways to wear shorts. So we decided to do what we do in most sartorial situations, turn to the street style set. As with every other piece of clothing, street stylists have some truly unique ways to wear shorts. From rocking shorts suits to colorful leather iterations and even bike shorts (yup, they’re still a thing), there are all kinds of new ways to wear shorts we’re betting you never thought of. Plus, 2020 marks the return of the romper — an often underused and undervalued weapon in our spring and summer arsenal. When it comes to length, anything goes. From micro shorts with a more sporty feel to shorts that go down below the knees into almost culotte territory, the options are pretty endless. So go with whatever you’re comfortable with. Get ready to take notes. Check out the slideshow above to see 21 new ways to wear shorts from now straight through summer. Some ideas are so good, you’ll want to wear them around the house.

Ways to Wear Shorts Spring 2020 Update

Ways to Wear Shorts Spring 2020 Update #1

Wear your long shorts low so the high-cut sides of your bodysuit poke out — even under a blazer. Slip on leather open-back mules to cap off the ensemble.
Ways to Wear Shorts Spring 2020 Update #2

Colorful leather was everywhere on the Spring 2020 runways so try topping off brown leather shorts with a light turtleneck, an open button-down and a soft pink leather jacket. Platforms preferred, but socks are optional.
Ways to Wear Shorts Spring 2020 Update #3

Show your stripes twice by tucking a striped button-down and basic white tee into striped shorts. Just make sure the shirt and shorts are different colors. Strappy pumps or sandals FTW.
Ways to Wear Shorts Spring 2020 Update #4

Suit up this season with a pink blazer and shorts set teamed with a light-colored tank top. Block-heel pumps make the ensemble office- or video conference call-ready.
Ways to Wear Shorts Spring 2020 Update #5

While everyone is obsessed with Bermudas, short shorts will never really go out of style. Style an athleisure-leaning pair with a pastel top and a draped blazer. Classic kicks help reinforce the laid-back look.
Ways to Wear Shorts Spring 2020 Update #6

Who says you can’t celebrate sweater weather and shorts season simultaneously? Team a sleeveless knit with minty shorts for a seasonless spin. Add in quilted footwear to further highlight the pairing.
Ways to Wear Shorts Spring 2020 Update #7

Distressed Bermudas are a fun take on the current long shorts obsession. Simply add in a white tee and white jacket plus lug-sole shoes to round out the look.
Ways to Wear Shorts Spring 2020 Update #8

Many people don’t know how to style those draped long shorts, but pairing them with a structured one-shoulder top balances out the loose silhouette. Throw in textured pumps and you’ve got a lewk.
Ways to Wear Shorts Spring 2020 Update #9

Max Mara’s Spring 2020 collection was all about shorts suits so go ahead and embrace the trend. Work in a tie, a trend for Fall 2020, and neutral boots or pumps.
Ways to Wear Shorts Spring 2020 Update #10

Break out the bandeau and wear it under a boxy blazer so you can cover up all that skin when you’re feeling shy or when the weather refuses to warm up. Add in colorful Bermudas and toe-loop sandals for a polished ensemble.
Ways to Wear Shorts Spring 2020 Update #11

Just like a statement belt can do wonders for a coat, it can also turn a simple white tank and long leather shorts into an outfit. Keep your sandals minimal to keep the focus up top.
Ways to Wear Shorts Spring 2020 Update #12

Don’t underestimate the power of a good romper. Slip one on over a blue button-down for an easy-peasy outfit. Combat boots or stylish ankle boots are the best way to round out the look.
Ways to Wear Shorts Spring 2020 Update #13

Aren’t you glad you kept those frayed jean shorts? Whether you bought them that way or simply took some scissors to a pair of old jeans, they’re a great contrast to a white tee and cropped statement jacket. But don’t overdo it — stick with streamlined sandals to finish off the look.
Ways to Wear Shorts Spring 2020 Update #14

Back in the 80s and early 90s, sporting bike shorts under dresses was a way to preserve modesty. Cut to 2020 and teaming them with a structured peplum top redefines the once-popular trend.
Ways to Wear Shorts Spring 2020 Update #15

Wearing colorful leather shorts is a cinch when you add in a logo belt. Tuck a plain white tee into them and wrap up the look with a leather jacket and leather boots or sandals.
Ways to Wear Shorts Spring 2020 Update #16

A front-and-center cut-out balances out all the leg you’ll be showing thanks to those bleached denim shorts. We recommend switching out the heavy black boots for platform sandals.
Ways to Wear Shorts Spring 2020 Update #17

Biker-style short shorts are already edgy so tame that toughness with a billowy top. Meet in the middle with a pair of snakeskin ankle boots.
Ways to Wear Shorts Spring 2020 Update #18

Animal prints are still a thing for spring so tuck an open shirt into denim cutoffs. Just make sure you pick out a full-coverage bra or bandeau you’re comfortable with everyone seeing. We’ll leave the shoes up to you.
Ways to Wear Shorts Spring 2020 Update #19

A split-sleeve top lets you go with the flow whether the weather is in the low 60s or mid 70s. Tuck it into a pair of belted shorts and cap off the look with neutral footwear.
Ways to Wear Shorts Spring 2020 Update #20

Double denim works just as well with jean shorts as it does jeans. Top off short shorts with a denim blazer in the same shade, then jazz up the look with stark sandals.
Ways to Wear Shorts Spring 2020 Update #21

A cropped white shirt and dark denim shorts equals one winning combo. Nod to both colors by sporting two-tone flats.