The Definitive Guide of What Shoes to Wear With Every Type of Shorts

A stylish pair of tailored shorts will take you from your desk to happy hour in a snap. Keep them office-appropriate during the day with flat slides or loafers, and come 5 o'clock, swap out your work shoes in favor of options with whimsical accents like feathers or tassels. The fun, embellished footwear will help balance out the structured shorts outside the office.

Gianvito Rossi Heels ($473, originally $945)

Topshop Sandals ($75)

Zara Slides ($20, originally $30)

Saint Laurent Slides ($595)

Gucci Loafers ($730)

Church's Loafers ($550)

Since denim cutoffs are likely your go-to off-duty shorts, pair them with shoes that you can run around in. Sleek sandals and fancy flats will get you to backyard BBQs and outdoor soirées with ease. If you're headed to a music festival, wear them with cute chelsea boots to keep your feet protected.

Madewell Sandals ($60, originally $98)

Diane von Furstenberg Sandals ($198)

Schutz Flats ($170)

René Caovilla Flats ($565, originally $1,130)

Sam Edelman Chelsea Boots ($100)

Chloe Chelsea Boots ($390, originally $975)

High-waisted shorts are great because they make your legs look long and lean. Elongate them even further with summery espadrille wedges or sky-high stilettos. Love the look of high heels but can't deal with the pain? Try a cute kitten heel instead.

Castaner Espadrille Wedges ($120)

See by Chloé Espadrille Wedges ($190)

Tibi Kitten Heels ($219, originally $525)

Charles David Kitten Heels ($118)

Dolce & Gabbana Stilettos ($2,575)

Alexandre Birman Stilettos ($346, originally $495)

Leather shorts up the cool factor of any outfit. Dress them up with low-block heels or trendy mules. Or pair them with matching leather booties for a sleek, coordinated look.

Report Heels ($30)

Pedro Garcia Heels ($198, originally $495)

Manolo Blahnik Mules ($955)

Sergio Rossi Mules ($650)

Dorateymur Boots ($546)

Steve Madden Boots ($130)

Bermuda shorts are a popular silhouette because not only do they look chic and polished, but they're totally versatile too. Keep them casual with sneakers, or make them look more pulled together with ballet flats or lace-up heels.

Adidas Sneakers ($140)

Greats Sneakers ($199)

Repetto Ballet Flats ($133, originally $295)

J.Crew Ballet Flats ($45, originally $90)

Missguided Heels ($37)

FashionNova Heels ($20, originally $35)

Do you love to show off your legs in short shorts? Make your pins look even longer by pairing the itty-bitty bottoms with modern pumps or flesh-toned heels. If flats are more your thing, ground the tiny shorts with a cool pair of chunky sandals.

Saint Laurent Pumps ($995)

Paul Andrew Pumps ($448, originally $895)

Stuart Weitzman Heels ($398)

Sam Edelman Heels ($120)

Loeffler Randall Sandals ($295)

Jil Sander Sandals ($399, originally $665)

Believe it or not, biker shorts are having a cool fashion moment this Summer. If you need a little sartorial inspo when it comes to styling them, just look to Kim Kardashian, who has worn them with shoes like thin-strap heels, dad sneakers, and PVC sandals.

Express Heels ($42, originally $70)

Vince Camuto Heels ($280)

Chloé Sneakers ($620)

Calvin Klein Sneakers ($127, originally $640)

Yeezy Heels ($603)

Kendall + Kylie Heels ($130)

The longer baggy board shorts you wore in the early aughts are popular again. Make them look sleek and modern by pairing them with a toe-ring sandal or a chunky heel. Or you can always toughen up the casual bottoms with a pair of lace-up booties.

Marc Jacobs Boots ($395)

Jimmy Choo Boots ($398, originally $995)

Forever 21 Sandals ($13)

Tory Burch Sandals ($248)

Tod's Heels ($398, originally $795)

Neiman Marcus Heels ($56, originally $199)