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 [1], but so will longer, mid-length silhouettes and Bermuda shorts. Read: there's a pair to suit you just waiting to be styled [2]. Need convincing? Read on for 41 ways to wear your shorts right, right now (or, ahem, when it's not quite so cold outside).
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.
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 [3] 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.