There are two types of garments I’ve avoided so much as attempting to style: harem pants and long shorts. And while my cowardice still prohibits me from donning a drop-crotch, this spring, I’m ready to venture out of jorts territory and into the land of Bermuda, cargo, and tailored shorts. Armed with an arsenal of Pinterest inspiration, I am ready to make the case that long shorts can, in fact, be both practical and stylish—and, perhaps even a work-appropriate option for warmer weather. Here are three looks to convince you that long shorts are not just for high school camp counselors and tropical cruise passengers.
Tailored Shorts + Blazer + Boots
Photo: Edward Berthelot/Getty Images
A matching blazer and tailored shorts set were not on my sartorial bingo card for this year, but this look has completely opened my mind. Pairing the set with a turtleneck and boots adds the cool-girl element and the fishnets are a fun, funky addition.

Trinity Double-breasted Blazer

Ryerson Silk-linen Bermuda Shorts

Ex-Ray Quilted Coat

Arco Sleeveless Turtleneck Cashmere Jumper

Cassetto Leather Knee-high Boots

Transparent-design Rectangle-frame Sunglasses
Cargo Shorts + White Jacket + Unexpected Shoe
Photo: Christian Vierig/Getty Images
If you are ever in a style rut, my favorite piece of advice is to start pairing things that don’t typically go together—a T-shirt over a cocktail dress or an informal tennis shoe with formal, tailored trousers. In this case, it’s a cargo short with a hot pink pump. It’s Bob the Builder meets Barbie, in the best way.

V-neck Tank Top

Concealed Front Fastening Denim Jacket

Linen Pleated Bermuda Shorts

Small Vsling Grained Texture Tote Bag

Elinor 65mm Slingback Pumps
White Bermuda Shorts + Black Button-Down
Photo: Robert Kamau/GC Images
Bella Hadid is a master of demonstrating that traditionally unflattering clothes can actually be quite flattering. While 95% of this is due to her being Bella Hadid, I think this particular outfit is universal. A good black and white pairing is eternally chic, and boots, sunglasses, and the right bra gives the look a tasteful edginess.

Knee-length Cargo Shorts

Square Neck Vest Top

Long-sleeve Buttoned Shirt

Pull-on Leather Boots

Oval Sunglasses

