Photo: Chris Craymer

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Shear Genius
You can't go wrong with a shearling—it's classic and so cozy. This knee-length version nips in at the waist, while fitted sock booties streamline the legs for a flattering silhouette overall. "It's almost like these pieces are giving you a hug," says O creative director Adam Glassman.

Coat, Ugg, $1,995. Sweater, Reiss, $265. Leggings, Spanx, $98. Boots, Gianvito Rossi, $1,095.