The anorak made its name as a weekend standby, but with detachable faux-fur trim, a drawstring waist, and slim-fitting cotton fabric, it becomes an unexpectedly chic choice for evening. "Throw it over a cocktail dress or dinner outfit," says Glassman, "and you're fabulously good to go."
Coat, H&M, $129; HM.com for stores. Dress, Muse, $179; Dillards.com. Purse, Stella McCartney, $885; NeimanMarcus.com. Earrings, Kara by Kara Ross, $175; Nordstrom; 800-695-8000. Necklace, Gerard Yosca, $395; Yosca.com. Bracelet, Giles and Brother, $175; GilesAndBrother.com. Heels, J. Crew, $275; JCrew.com.