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