Your 2019 Guide to the Best Summer Shorts is Here

Who said shopping for shorts had to be hard?

By Phoebe Neuman
cute summer shorts w paperbag waist

I’m the first to admit that I have a bit of a Goldilocks complex when it comes to shorts. The hunt for a pair that aren’t too short, aren’t too tight, and are just right seems to never end—so much so that last summer I swore them off all together in favor of flippy dresses and breezy linen pants. But this summer I’m determined to get it right, and have scoured the internet in search of the perfect pairs. The following 25 shorts made the cut—and we’ve got some in every style (from sporty to sweet and beyond) and body type. Picnics and beach volleyball sessions, here we come!

featured image by kristen kilpatrick

High Waisted

High-waisted styles are always my go-to, and shorts are no exception. The following five pairs are some of the most figure flattering on the market, and thanks to their figure-flattering waists and roomy legs, are ultra-comfortable as well.

Madewell Striped shorts

Paperbag Shorts in Rainbow Stripe, Madewell

asos gignham shorts

Lilac Gingham Utility Short, ASOS Design

Revolve shorts

Parker Carlo Short, Revolve

Anthropologie shorts

Marie Frayed Shorts, Anthropologie


If you have a spring wedding or a dressed-up brunch on the books, you can’t go wrong with a sharp pair of shorts. With tailored cuts and bold prints, the following styles can all be dressed up with a pretty blouse and killer heels (you’ll earn extra styling points for throwing a blazer on top, too), but will also look great with fresh sneakers and a graphic tee.

Reformation rossi shorts

Rossi Short, Reformation

ulla johson shorts

Ulla Johnson Martim Shorts, Shopbop

Lovers + Friends sorts

Lovers + Friends Analee Short, Revolve

Eloquii shorts

Printed Short, Eloquii

Black Shorts

City Chic Sweet Frill Shorts, Nordstrom


If you’re looking for comfort, athletic-inspired styles are the place to start. Though each of these pairs could see you through a gym session or a morning hike, don’t be afraid to pull a few styling cues from your streetwear-savvy friend by styling them up with heels and your favorite going-out top.

madewell yellow shorts

Madewell Pull-On Shorts, Nordstrom

Urban Outfitter shorts

Eve Striped Drawstring Short, Urban Outfitters

nike women's shorts

Nike ACG Women’s Shorts, Nordstrom

herschel shorts

Herschel Supply Co. Printed Voyage Alta Short, Urban Outfitters

Lululemon sweat shorts

Hello Sunday Short, Lululemon


Like their high-waisted sisters, pleated shorts are flattering on every body type thanks to the typically roomier cut they feature through the legs. Go for styles in stiffer cottons or linens for a safari-inspired look, or pick up a pair in breezy crepe to get the look of a skirt—minus the potential for any wardrobe malfunctions.

Club Monaco shorts

Club Monaco Darcee Shorts, Shopbop

& Other Stories Shorts

High-Waisted Linen Blend Shorts, & Other Stories

utility shorts

Citizens of Humanity Cassidy High-Rise Shorts, Anthropologie

J.O.A. shorts

J.O.A. Pleated Waist Tie Short, Revolve

Free People Shorts

Procida Shorts, Free People


It’s hard to think of a bigger summer staple than a pair of denim cutoffs. But, if you’re anything like me, these styles can feel like hardest to pull off. The trick I’ve discovered to avoid pairs that ride up or feel too restrictive when you sit down? Size up. It will give the pair that vintage look, and will ensure you can wear them all day long.

topshop denim shorts

Topshop Roll Cuff Denim Mom Shorts, Nordstrom

Denim Shorts

Levi’s 501 High-Rise Denim Shorts, Free People

Good American denim shorts

The Bombshell Short, Good American

AGOLDE denim shorts

AGOLDE 90s Short, Revolve

paige denim shorts

Paige Margot High Rise Cutoff Denim Shorts, Nordstrom