The Winter of Our Content-A Head-to-Toe Style Guide

"Sturdy boots with a good tread are a great investment," said Beltempo.

Best Foot Forward

She favors insulated, weatherproof takes with "thick, rubber soles that keep you off the ground." Barron agrees, citing her clients' dedication to the Row's front-zip leather ankle boots, which have sold out every season since they launched in 2019. To replicate the look, which Barron describes as "sleek enough to wear with anything from dresses to jeans," seek out durable alternatives with lower price tags.

For another smart, wallet-friendly option, don't discount proper hiking boots-their functional allure needn't be reserved for Bear Grylls on a bushwhack. Adventure-focused brands like Diemme and Sorel (both have collaborated with luxury labels from Cecilie Bahnsen to Proenza Schouler) offer waterproof, grippy styles that guaraNtee you won't do battle with a slippery subway staircase. Beltempo suggests wearing them with thick tights, paired with feminine-leaning skirts or dresses for a fun contrast.

"If you add a chunky sock, match its color to your boot or stocking for visual cohesiveness." Got your eye on an unlined pair? Rohe recommends adding a sturdy wool or shearling insole to amp up the warmth. Bonus tip? Insoles are a great way to keep your fall flats in rotation for longer, says Rohe, who slots a fuzzy layer into her more nimble loafers on chilly, snow-free days.

Whether you go for Gore-Tex or suede (in which case, a water-repelling spray is your best friend), Leibowitz advises getting a pair half a size bigger than your standard size to leave room for thick socks, and "for the heat to circulate [around] your feet."

Head Starts

This season, new head coverings are challenging the beanie's dominance in the status quo. "We've seen triangle scarves and balaclavas take center stage," said Kay Barron, fashion director at Net-a-Porter.