Is there anything less sexy than winter dressing? It’s so easy to just say yes to pants and leggings every day that my winter look may as well be a seasonal portmanteau — peggings. Each leg swaddled in thick, standard-issue American Apparel tights that cover every square inch of leg, black tubes unceremoniously stuffed into too-thick socks. (Thick socks, the archnemesis of cute shoes — but that’s another saga.) Cold weather means covering up and trudging through, and my winter outfits reflect an impulse to endure; it's survival of the fittest, not the best-dressed. If I’m not careful, I end up peggings-ing all winter. In an effort to avoid this, I shop. In an effort to stick to a budget, I don’t buy anything. Thus peggings happen. It’s a vicious cycle.I’ve resolved that this year will be different. This year I have discovered the secret to winter dressing that’s made all the difference for me: When temperatures go low, take your pant hems high. Cropped, cuffed, or roughly cut, pant hems should embrace your winter boots — show a little stockinged or brazenly naked ankle. All these years I’d been taking for granted that a good boot just needs a little breathing room; a cropped silhouette offsets the humdrum look of skinny jeans into black boots.The secret revealed itself to me in a consignment shop when I stumbled upon Hope’s Macy boot in my size. I tried it on with three or four different coats, each one creating a new shape and silhouette that excited. The boot is tinged with biker-babe credibility, a Rick Owens-lite sensibility that pairs well with lots of denim. The heel isn’t as chunky as I’d like, but the boot is so good in every other way that I came under its spell. There is something Vetements-y about the way the boot articulates itself, almost as if it takes up more space by giving me less to stand on. It’s a little terrifying but surprisingly comfortable.