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How to Wear Shorts

How to Wear Shorts Anywhere — That's Not the Gym or a Festival

Jan 28 2019

I've struggled for the better part of a decade to make shorts look cool. Chop a pair of trousers off 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 the beach? The truth is: they really are just like trousers, but withs lots of warm weather potential — especially when you factor in the many styles to choose from. Cycling shorts and athletic varieties will play a big part in the Spring '19 lineup, but so will longer, mid-length silhouettes and Bermuda shorts. Read: there's a pair to suit you just waiting to be styled. Need convincing? Read on for 41 ways to wear your shorts right, right now (or, ahem, when it's not quite so cold outside).

Image Source: Getty

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

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

Throw a button-down on 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.

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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 cyling shorts more sophisticated, less sporty.

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

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

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

Give cycling 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 makes these mid-length shorts office appropriate.

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

A duster and boots breaths 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 cosy jumper.

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

Lean into the sporty feel of your cycling shorts with dad sneakers and a bum bag.

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.

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

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

We're partial to boots, blazer, and cycling 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 nine-to-five style.

Elevate gym separates with the right, statement-making outerwear.

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

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

Keep it simple with a button-down in a bright hue and a well-fit 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.

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