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Margot 75

$288 ($575)
Buy at stuartweitzman.com

Sock booties are year-round fashion fixtures, and the Margot 75 is a luxe spin on the most-wanted silhouette. Crafted from suede, nappa or stretch canvas and anchored by a cylindrical block heel, these minimalist ankle boots are an easy choice with deconstructed tailoring. Throw on your favorite overcoat and go.