Here's How All the Cool Girls Will Be Wearing Their Leggings This Winter
If you still think leggings are reserved for lazy Sundays and workout classes, think again. This winter, the cool-girl approach is giving the stretchy staple a serious upgrade. Instead of basic black paired with oversize hoodies, we’re seeing sleek iterations styled with elevated outerwear and tailored layers—even stirrup leggings tucked into pointed-toe boots, puffy coats cinched at the waist, and cozy yet polished knits. It’s about contrast: combining comfort with a sharply edited eye for proportions.
The secret to pulling them off this season lies in the styling. Darker neutrals in luxe materials instantly read more fashion than fitness, especially when balanced with statement outerwear like a shearling jacket or a long wool coat. Accessories do the rest of the work—add a sleek crossbody, sculptural earrings, or slim sunglasses, and your legging outfit suddenly feels like something straight from a Paris street style roundup rather than your morning coffee run.
And perhaps the best part? They’re practical. Whether you’re layering them under a maxi coat for a day of errands or pairing them with heeled boots for an evening out, this winter’s legging outfits marry ease with sophistication. The takeaway is clear: The cool-girl uniform may still include leggings, but they’ve never looked—or felt—so elevated.
See some of the coolest winter legging outfits below and shop the essentials along the way.
Get the look: Trench jacket + Leggings + Ballet flats
Get the look: Zip-up jacket + T-shirt + Leggings + Suede ballet flats
Get the look: Black trench coat + Oversize sweater + Leggings + Pointed-toe flats
Get the look: Long jacket + Turtleneck + Plaid shirt + Leggings + Tall boots
Get the look: Leather jacket + Sweater + Leggings + Loafers
Get the look: Shearling zip-up jacket + Leggings + Tall socks + Clogs
Get the look: Puffer coat + Leggings + Tall leather boots
Get the look: Oversize tan blazer + Sweater + Leggings + Tall socks + Sneakers
Get the look: Suede jacket + Sweater + Leggings + Tall socks + Uggs
Get the look: Quilted coats + Sweater + Leggings + Tall boots
Get the look: Quilted puffer coat + T-shirt + Leggings + Sneakers
Get the look: Zip-up jacket + Leggings + Socks + Sneakers
Get the look: Faux-fur coat + Minidress + Leggings + Flats
Get the look: Leather jacket + Thin sweater + Leggings + Sneakers