38 Cool Ways to Style Shorts, Because They're Coming Back For Spring

Updated on 2/5/2019 at 11:10 AM

I've struggled for the better part of a decade to make shorts look cool. Chop off a pair of pants at the knee (or the thigh) and double the insecurities and the questions — how do I wear these to the office? Out to dinner? Anywhere that's not a music festival? The truth is, they really are just pants, the kind of pants with lots of potential — especially when you factor in the many styles to choose from. Biker shorts and athletic varieties will play a big part in the Spring '19 lineup, but so will longer, midlength silhouettes and Bermuda shorts. Read: there's a pair to suit you just waiting to be styled. Need convincing? Read on for 38 ways to wear your shorts right, right now.

Dress up a throwback look with heels. If you're feeling a little intimidated by shorts, know that the heels help elongate and flatter your gams.

Balance proportions and give biker shorts a chic finish with a puff-sleeve top.

Throw on a button-down with your cutoffs, then give it all a boost with heeled mules.

Give a short suit a shot and see just how sophisticated it can be.

Pair short shorts with a blazer and flats to give them more polish.

Top a pair of Bermuda shorts with a cropped top and style with boots for a look that goes beyond Summer.

Slip into a pair of slides and add a blazer to make biker shorts more sophisticated, less sporty.

A suit looks way cool in a laid-back cut.

Denim shorts with a breezy tank will forever be a go-to outfit when the weather warms.

Give jean shorts some edge with an asymmetrical or tunic top and pretty heels.

Give biker shorts a minimalist vibe with understated pumps and a chic pullover.

Polish up your short shorts with a tweedy blazer and flats.

Reinvent sporty shorts with strappy heels and a tuxedo jacket.

Khaki shorts never looked this cool. Edge them up with lace-up boots.

Cowboy boots and a duster will transform your basic shorts.

A sophisticated blazer and kitten heels make these midlength shorts office appropriate.

Reimagine sporty vibes with a quirky button-down and dad sneakers.

A duster and boots breathe new life into a pair of short shorts when the weather cools.

Belt a coat over your shorts if you're feeling the need for more coverage.

A romantic top instantly elevates a pair of shorts — especially when tucked in and belted.

Warm up a pair of long shorts with a cozy sweater.

High-waisted shorts are a chic alternative to a miniskirt.

Lean into the sporty feel of your biker shorts with dad sneakers and a fanny pack.

Remix a short suit with a pair of combat boots.

Go for the full-on sportif look in a coordinating tracksuit, then pare it down with a clutch and a trench coat.

Biker shorts and a windbreaker look decidedly cooler with a fresh pair of ankle boots.

Biker shorts are ultraflattering when worn with heels and a blazer belted to show off your waist.

We're partial to boots, a blazer, and biker shorts for a cool alternative to your weekend brunch look.

Swap your pencil skirt for a pair of culottes if you're looking to refresh your 9-to-5 style.

Elevate gym separates with the right statement-making outerwear.

We love the simplicity of this all-black look, especially since the biker shorts add just the right outfit intrigue.

Distressed shorts pair so perfectly with a well-worn sweater and heels for that effortless aesthetic.

Keep it simple with a button-down in a bright hue and a well-fitting pair of denim cutoffs.

Remix your matching separates and opt for a pair of shorts with a coordinating trench coat.

Swap denim cutoffs for a pair of tie-waist shorts that you can wear by day or night.

Channel your inner Kim Kardashian in a luxe duster and accessories to dress up your basic bottoms.

Give shorts a longer life when cold weather hits by layering tights underneath.

Say yes to coordinates that look this cool, then finish with a coat and boots for transitional weather.