Play up your makeup when wearing borrowed-from-the-boys looks.
"I gave Stephanie a really glossy pink lip [Elizabeth Arden Beautiful Color Luminous Lip Gloss in Passion Fruit, $18; ElizabethArden.com] because I love the juxtaposition of the girly color with her menswear-inspired outfit," says makeup artist Rebecca Restrepo. "In more feminine outfits, I'd keep her makeup matte and understated."
Sweater, Comptoir des Cotonniers, $280; 212-460-5289. Striped shirt, $195; ThomasPink.com. Pants, Sportmax, $425; 212-674-1817. Bar necklace, $90; VitaFede.com. Bow tie, $60; ThomasPink.com.