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.
I wear them with cutoff Levi’s 501s, the ones I’d paired with loafers in the summer. The effect is startling: I am transformed. The rough hem of the jeans inelegantly grazes the tops of each boot; a hint of Hansel From Basel trouser sock peeks out. It’s very “Kate Hudson looks on appreciatively while Ryder learns guitar,” and I like it. I untuck my striped Brooks Brothers shirt and reach for a threadbare band tee. I burrow deeply into every oversize coat I can find and marvel at my newfound slouchy confidence; in the era of Demna, inelegance is the new elegance. The narrower heel elongates my stubby legs, and suddenly puffy parkas don’t seem so daunting. (Good thing Uniqlo’s newest collaboration with Christophe Lemaire features such a cute one.) Then there are the Céline Chelsea boots. They are 60% off and (sort of) in my size. I reach for my clavicle in astonishment, looking for someone to turn to and corroborate my experience, this moment — can you see me? In these shoes? Am I really here? I hunt down the nearest mirror and reach out to myself through space and time, a hand brushing aside self-doubt to say, “You have manifested in this realm.” Subsequently, $500 manifests itself out of my bank account, but that’s beside the point. I wear them with my Not side-pleat pants, the ones I thought were best suited for spring and summer’s sandal weather and the impostor Acne babouches I picked up on sale. The boots are tall; the wide pant leg engulfs their upper reaches for a very Comme-ing effect. (Pun intended.) The hunt continues — though the budget concerns remain. At least now I have an idea of what I’m looking for, a way to fix the frosty frumpies. I still embrace my peggings past, but know that this winter I have a well-heeled future ahead of me.