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; ShopBop.com. Dress, Black Fleece by Brooks Brothers, $975; BrooksBrothers.com. Bag, Kooba, $248; Kooba.com. Tights, Bootights by Shelby Mason, $32; Zappos.com.
Right: Boots, Fratelli Rossetti, $720; 212-888-5107. Coat, Ella Moss, $278; EllaMoss.com. Shirt, Osklen, $347; 212-219-8250. Skirt, DKNY, $295; DKNY.com. Socks, Falke, $24, The Sock Hop; 212-625-3105.