I’m Sick of Seeing the Same Winter Leggings Outfits—5 Ways To Wear Them That’ll Look More Chic

For those crisp mornings when you wake up already feeling behind and can’t bear to part ways with your cosy Olivia Von Halle pyjamas or If Only If night dresses, leggings arrive as a quick-fix solution to not only help you remain comfortable throughout the day, but also look incredibly chic. An antidote to the winter chill that sets in this time of year, leggings are a substitute for the sumptuously decadent loungewear styles we dream of wearing all day long.

While they’re no match for bundling up in your flannel duvet and snuggling into a pair of bed socks à la Bridget Jones, leggings prove a more socially acceptable way of serving the perfunctory requirement of staying warm and looking good. (Two of the most crucial things on Maslow’s Hierarchy of Needs.)

And while I love a leggings outfit as much as the next person, I do have one slight problem with them. Because of their very elementary nature, I tend to feel like the chicest leggings looks can often feel a shade repetitive. Even as someone who has made a career of identifying and reporting on the latest sartorial happenings, I, too, fall into the trap of finding an ensemble formula that works, which has lately been teaming cropped leggings with a boxy high-neck knit and ruched loafers, and wearing it until the silhouette feels exhausted. A proud outfit repeater at heart, a quality that speaks to my sustainably minded approach to fashion, there’s, of course, nothing inherently wrong with this. But this season, I want to lean into dressing up more and challenge myself to be a bit more intentional about what I wear—yes, even a basic as affordable and accessible as leggings.