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1. THE BELT
Take the Goldilocks approach to your everyday belting needs: too thin will cut you in half; too thick screams champion prizefighter. Find the just-right midrange size like Will Leather Goods’ classic saddle belt ($90) in a neutral shade. Buckle tip: pick the metal you prefer for jewelry.
2. THE GLOVES
Keep hypothermia at bay with stylish finger covers like Tanner Goods’ timeless, soft-as-butter deerskin utility gloves ($85). They’ll age gracefully while warming and protecting those precious digits with sumptuous merino wool lining.
3. THE HAT
All hats are not created equal. The crown should fit snugly, but shouldn’t be tight enough to affect circulation. Infuse just a touch of boho into your wardrobe with Nordstrom’s chic floppy wool felt hats ($38). A double-duty accessory piece, the soft wool keeps your head warm in all weather while the swishy brim frames your best asset.
4. THE BOOTS
Boot trends are hard to track, as heights rise and fall capriciously. Our sage advice: avoid anything that says “jester” or “jouster.” Chio’s Beckam Boot ($315 at Halo) finds that sweet spot, with a stacked heel that elongates the leg but is plenty sturdy for a wintry stomp down Broadway.
5. THE SCARF
Colors and textures abound, and they’re pretty much all fair game—the key is how you tie it up. If you tend to default to the Amelia Earhart look (please don’t), do yourself a favor and opt instead for the ease of an infinity scarf, like this super-soft Sherpa fleece version from Reif ($46 at Backtalk) in a neutral color like cream that goes with everything.
6. THE BAG
A tiny, glittery clutch might be perfect for a night on the town, but city living requires a tote that can shoulder some urban ballast. Local line Ellington’s durable Eva Satchel ($319), made from glazed Italian lamb leather with brushed nickel hardware and multiple interior pockets, is up to the challenge.