Olivia Palermo, socialite
"Overdress rather than underdress."
Buy a great oversize clutch that works for day or night. Keep double-sided tape in your bag to shorten a hem in a pinch. Mix hard and soft, masculine and feminine. Overdress rather than underdress. Forget red and green for the holiday season — too predictable. Try platform heels, which look hot but put less stress on your arches when you're standing all night at a party. Play with hot pink. Pack baby powder to absorb oil from both your hair and face. Load up on heavy gold jewelry. Invest in a long winter coat for evenings so your bare legs aren't exposed.
On Palermo, left: Blazer, $79.50, The Limited; dress, $660, Diane von Furstenberg; booties, $790, Dior; belt, $216, Linea Pelle Collection; bracelet, $113, Giles & Brother by Philip Crangi; ring, $185, Rosena Sammi; Palermo's own necklace. On model, right: Top, $595, Vera Wang; skirt, $995, Rachel Roy; shoes, $550, Boss Black; necklace, $1600, Subversive Jewelry by Justin Giunta.
Dress $630, Philosophy di Alberta Ferretti; (212) 460-5500. Belt $120, Linea Pelle Collection; ronherman.com