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Winter’s technically still a month away, but the wind chill doesn’t heed dates. We were already feeling it deep in our bones this week in New York. We’ve recently tackled transitional coats, and today we’re focusing on another wardrobe essential for staying warm—shoes! We’re calling it a shoe wardrobe because we’re talking about a four-month span of time (at least!) when we’ll go from cold, to rain, to snow, to (ugh) melted snow and slush, which all call for different styles of shoes, and also because, well, much like George Costanza, we also dress according to mood, so we need to have a few pairs that can meet us where we are at any certain time.
We’ll begin with the classic: a winter boot—or rather, winter boots. Depending on your personal style, you may want to start with classic knee-high smooth leather boots, a great every-day option if you favor a skirt, and also the perfect choice for more dressed-up holiday parties. I’m a big fan of retro styles with an almond toe and a sensible mid heel, and luckily it seems many designers have been modernizing the silhouette this season. The over-the-knee gathered shaft in this Proenza Schouler style makes it a little subversive, but the 2.5 inch heel makes it truly ready for every-day, while a flat version by Khaite hints at a riding boot with its trapezoid toe. Then of course, we have the made-to-grind, ass-kicking category of boots; this is where the classic Dr. Martens lace-up style comes in (consider a short lace-up in bottle green, or the Rick Owens collaboration with a thick platform and extra-long shoe laces to wrap around the ankle). Motorcycle boots also fit into this category—whether you go with the iconic Fry style (did you know they even make them in pink?), or with a more upscale take on it, like this brown suede version (the color is called Fondant) by Bottega Veneta.
Ankle boots, meanwhile, work with both pants and skirts. As versatile as they are, you might as well get a little adventurous and play with fun textures like shearling, which—guess what?—also keeps you warm! Consider shearling-lined No.6 clog boots, Phoebe Philo’s kinda goth (in a good way, obviously) flatform Bumper Booties, or the shearling-on-the-outside desert boots from Le Monde Beryl.
Beyond boots you may want something a little chunky—like Simone Rocha’s remix of an oxford/monk strap shoe, Prada’s ruby red loafers, or 3.1 Phillip Lim’s lug-sole Mary Janes, which are begging to be worn for luxe ribbed tights or thick marled socks. (Bonus tip, consider sizing up a half-size if necessary to fully accommodate your cozy ensembles.)
All that said, if you live for a non-shoe shoe, you don’t have to forgo your proclivities entirely. Queens of the look Ashley and Mary-Kate Olsen of The Row make a dainty shearling-lined flat, and Alaïa also does its iconic Mary Jane in merino shearling. If you score one or two styles from this list, you’ll be able to fashionably survive the winter doldrums.
