Most staple items in your closet, like denim, dresses and tees, can easily transition from season to season. But others just aren’t that versatile. Chunky knits in the middle of summer? Probably not. Shorts after December 1? Well, actually, yes. It might seem counterintuitive, but these leg-baring numbers can totally be hacked for the cold weather just like favorite skirts and frocks. All you need are a few good pairs of tights (patterns and glitter are highly encouraged) and a little sartorial know-how, which we’re sharing right here. Gather a little style inspo from these five getups and put your shorts back to work.

How to Wear Leather Shorts in Winter


Leather shorts are substantial enough to brave the chill of the season. Play up their rugged vibe and pair them with thick ribbed tights, boxy chambray and a fuzzy buffalo-check coat.

COS Leather Shorts ($350), M.i.h. Seberg Top ($245), Steve Madden Sweater Bootie ($170) + Just Female Wood Wool Coat ($187)

How to Wear Jean Shorts in the Winter


Yes, you can wear your denim cut-offs in the cold. Show off your gams in sheer and sparkly tights + chunky-heeled booties and top off with an of-the-moment turtleneck and faux fur vest for a winterized festival look.

Mother Denim Loosey Fray Shorts ($145), Ann Taylor Cashmere Colorblock Sweater ($229), Topshop Sleeveless Faux Fur Hybrid Coat ($150) + Ateljé 71 Veda Velcro High Heeled Booties ($279)

How to Wear Wool Shorts in the Winter


Wool shorts are the trendsetter’s answer to standard suiting and a rad way to freshen up your nine-to-five repertoire. Workplace polish comes in the form of a structured collared shirt and black or jewel-toned tights. An oversized knit will take on too-cold cubicles with force.

Mango Flecked Wool Short ($60), BDG Madeline Pullover Sweater ($98), COS Long Contrast Panel Shirt ($99) + Topshop Josephine Flare Heeled Leather Shoes ($110)

How to Wear Embroidered Shorts in the Winter


Your night out get-up just got way more interesting with these luxe-looking velvet shorts. Wear with a thin long-sleeve top and ditch your heels for a warm pair of over-the-knee boots. Complete the alt-folk look with a mohair cape that’s cozy but definitely not bulky.

Free People Love Last Embroidered Shorts ($98), H&M Glittery Top ($50), Sam Edelman Rylan Over-the-Knee Boot ($250) + ASOS Poncho in Brushed Mohair Check ($76)

How to Wear Plaid Shorts in the Winter


Go preppy-chic with these plaid wool shorts and a professor-approved houndstooth blazer. A chambray and riding boots will round out the collegiate feel, or you could upgrade to a classic white button-down for a more refined look.

Gap Plaid Wool Tailored Shorts ($50), Ann Taylor Chambray Pocket Shirt ($55), M. Gemi The Pezzo Boot ($398) + Zara Houndstooth Jacket ($149)

Would you wear shorts in winter? Show how you do shorts by tagging us on Instagram + using hashtag #wintershorts.