pencil skirt

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Adam's favorite style, and for good reason: It's chic and flatters most body types. It's also a workplace staple, along with a crisp button-down.

What type of shoes it works with: Pointy flat, kitten heel, and t-strap heel.

From left to right: Pointy flat, Via Spiga, $185, Lord & Taylor, 800-223-7440. Kitten heel, Kate Spade New York, $328, T-strap heel, Tory Burch, $425, Skirt, Jones New York Collection, $99,