How Cool Girls Will Be Wearing Their Leggings This Winter

woman wearing winter legging outfit 2025

(Image credit: @chrystelleeriksberger; @ingridedvinsen)

published 19 November 2025

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.