Stephanie Phair
Photo: Sarra Fleur Abou-El-Haj
Missoni jacket: Original, $2,870; TheOutNet.com, $574. The easy cut—"a cross between a bomber and a cardigan," says Phair—works for the office or with jeans on weekends ("The chic shopper always asks, "How many ways can I wear this?"). Knits are smart for low-builk, no-wrinkle packing

Tomas Maier tank: Original, $205; TheOutNet.com, $105. A tank instead of a shirt "adds a more relaxed twist," Phair says. The trademark Missoni print on the jacket won't come off as loud of brash if you wear it with black.

RM by Roland Mouret skirt: Original, $1,235; TheOutNet.com, $371. "A pencil skirt is my go-to piece. A structured style and thicker fabric give you a better shape."

Brian Atwood shoes: Original, $1,035; TheOutNet.com, $414. Phair usually wears flats during the day and switches to pumps for evening: These wooden-heeled, woven-leather stilettos combine a classic shape with modern design.

Roberto Cavalli cuff: Original, $590; TheOutNet.com, $236. With a patterned jacket, you want simple jewelry like this classic-looking paneled bracelet.

Next: Stephanie explains her top shopping and web-surfing strategies