women in pleated skirts having drinks

Photo: William Garrett

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Pleated Skirt
This style flatters most body types. "It glides as you walk, leading the eye away from problem areas," says Adam.

How to Wear It: Choose a fabric with an easy drape, like silk crepe, and if you're thicker in the middle, make sure the skirt has a wider waistband. Top with blazers and knits; shoes should be delicate. Think stilettos, pumps with bow details, slingbacks, and T-straps.
If You're Short: Don't go shorter than knee length "unless you want to look like Britney Spears in the 'Baby One More Time' video," says Adam.
If You're Tall: Try a midcalf length for a '20s look.
What to Avoid: Any kind of boot, which will clash with the skirt's ladylike vibe.

Shirt, Tommy Hilfiger, $70. Jacket, Lauren Ralph Lauren, $260. Skirt, Kate Spade New York, $298. Watch, Michael Kors. Tights, DKNY. Shoes, CH Carolina Herrera. Sweater, 525 America, $48. Skirt, Trina Turk, $238. Watch, Movado. Stockings, Assets Red Hot Label by Spanx. Shoes, L.K. Bennett.

Shot at the John Dory Oyster Bar, New York City. These tasty cocktails—the Set Sail (left) and the Queen's Park Swizzle—are the NYC restaurant's signatures.

Next: 7 new fall skirts—plus the perfect shoes to pair them with