Photo: Chris Craymer

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Walk This Way
A stiletto-heeled boot will always be a wardrobe essential. Wear ankle styles with dark tights so you don't visually shorten the leg. Pair a tall boot with a skirt that hits at or below the knee—but if you have to wear a shorter skirt, opaque tights are a must.

Left: Booties, Elie Tahari, $595; 212-334-4441. Sweater and skirt, Cynthia Rowley, $295 and $325; for stores. Watch, Gossip for QVC; $48; Gloves, Bruno Magli, $270;800-624-5430. Bag, IIIBeca by Joy Gryson, $158; Tights, Bootights by Shelby Mason,$32;

Right: Boots, L.K. Bennett, $695; 713-961-0009. Coat, Tory Burch, $850; Sweater, H&M, $50; Tights, Bootights by Shelby Mason, $32; Shot on location at Ladurée, NYC.