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Photo: Chris Craymer

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Step lively in this season's gorgeous boots! We've rounded up the latest and greatest, including runway-inspired ankle stilettos, classic knee-high styles, edgy wedges, and yes, shbooties—along with tips on how to wear them all with flair.

A graphic black-and-white paddock boot gets even more playful when paired with socks. (If this look feels too young for you, opt for opaque black tights instead.) A patchwork play on menswear prints can also add zing to solid black outfits.

Left: Boots, Roger Vivier,  $2,395; 212-861-5371. Coat, Diane von Furstenberg, $598; Dress, Black Fleece by Brooks Brothers, $975; Bag, Kooba, $248; Tights, Bootights by Shelby Mason, $32;

Right: Boots, Fratelli Rossetti, $720; 212-888-5107. Coat, Ella Moss, $278; Shirt, Osklen, $347; 212-219-8250. Skirt, DKNY, $295; Socks, Falke, $24, The Sock Hop; 212-625-3105.