Styling shorts, whether denim cutoffs or biker shorts, isn’t always easy. So we tapped experts and scoured celebrity street style for inspiration. Here are 14 outfits with shorts to try.

Take your wardrobe to new heights.

From linen shorts to leather hot pants, summer’s favorite clothing item has an answer to every occasion. Denim cutoffs are a must for backyard barbecues and trips to the beach, while bike shorts, once reserved for workouts, evolved into a street-style staple. More recently, the underwear-as-outerwear trend has brought boxer shorts and teeny tiny micro shorts to the forefront. Fashion analyst and trend forecaster Mandy Lee discussed what’s next in a recent Instagram post, predicting that the rise of bloomers will soon give way to slik slip shorts gaining popularity.

Whatever shorts you reach for this summer, styling them isn't always easy. Managing to stay cool and look it is no simple feat. So we tapped experts and scoured celebrity street style to offer you inspiration. Ahead, find 14 outfits with shorts to try this summer.

Dressed Up Denim

A houndstooth jacket isn't the first thing you think to pair with a pair of denim shorts, but the combination looks surprisingly at home together, thanks in large part to the way red and blue compliment each other.

New York-based stylist Mario Horne. also recommends pairing denim shorts with a statement belt, button down, and penny loafers.

Short Shorts and a Button Down

"When wearing short, shorts I think it's very important that your proportions are on point," Horne says. To balance out a pair of short shorts, "You can never go wrong with an oversized crisp, white button up (loosely tucked in the front) and a statement belt. "

Short Shorts, Long Jacket

Another way to balance out a pair of micro mini shorts is to pair them with a long jacket. Penny loafers add a sophisticated touch.

Oversized Shorts and Riding Boots

Bella Hadid shows off her equestrian background by sporting riding boots, and proves that the "big pants small top" formula works with shorts too

Look of the day

Must see fits from all your favorite celebs. See the looks

Prep School Casual

Kendall Jenner strikes just the right balance of polished and laid back by pairing preppy elements (loafers and a blazer) with more casual ones (shorts and a baseball hat).

Athletic Shorts and an Oversized Jacket

Cherry red is the accent color of the season, and what better way to incorporate one than a pair of red shorts peaking out under an oversized black top? Matching accessories tie it all together.

White Denim with a Cardigan and Ballet Flats

Shorts go great with ballet flats. The combination feels like a fresh, updated take on the kind of bottoms we paired with the trendy shoe on its first go-around in the 2010s. Adding a cardigan on top makes the perfect polished outfit to throw on for errands or lunch.

Matchy Matchy Linen Shorts

Take notes from Meghan Markle, who paired a pair of beige shorts with a black tank, black belt, and a white sweater with black trim. The mix and match neutrals look put together but laid back.

A Canadian Tuxedo

For the simplest of outfit formulas, pair denim cutoffs with a white crop top and an oversized denim jacket, à la Hailey Bieber.

Dark Denim With an Open Button Down

A darker, more tailored denim short offers a more formal look, especially when paired with a crisp white button down and pointed toe heels. Keeping the button down largely unbuttoned and the cuffs open keeps the look from feeling too buttoned up.

Bike Shorts and a Blazer

“I also love mixing sportswear and evening wear pieces! I’d keep the look all black! Pair your black biker shorts with an oversized matching blazer ( with satin lapel ) layered over a lace corset and a pointy-toe kitten heel for a night on the town.”

A Short Suit With Sneakers

To style a short suit for a more casual setting, balance out the formality with a T-shirt and sneakers. Here, Bella Hadid shows us how to get the look—pairing a tweed blazer and matching shorts with a T-shirt and adding '90s elements with chunky sneakers, high socks, and tiny sunglasses.

Business on the Top, Soccer Practice on the Bottom

In the same way that a pair of sambas can dress down trousers or add interest to a sundress, athletic shorts balance out more tailored pieces. Adding kitten heels ties the whole thing together.

Knee Highs

Balance out all that leg with a pair of knee-high socks in the same color as your shorts—ballet flats and a blazer add to the schoolboy theme.