With a nipped waist and stylish pockets, this strapless dress just needs simple black pumps to look amazing. Isabella Oliver black bustier dress ($229); Nine West Rocha pumps ($79)
Who knew you could make it a wear-everywhere skirt? Slip on a leather bomber and your dress becomes a skirt. Add flats (they’re comfy but cuter than sneakers).
Ann Taylor top ($45); Members Only jacket ($250); Pour La Victoire Juliet flats ($200)TIP: The banded hem at the bottom of this jacket cinches your waist—so flattering.
Cover up—or cover under—for a more professional look. Layer the dress over a turtle-neck. Opaque black tights and Mary Janes complete the look.
Isabella Oliver gray classic turtleneck ($109); DKNY tights ($13.50); Nine West Zuri heels ($79)TIP: Tuck the turtleneck into your tights so it doesn’t bunch. Or, try a turtleneck bodysuit.
Show off the dress (but not too much skin) by adding a blazer. Stay warm and stylish in a blazer. Finish it off with fun pumps and a bold necklace.
Tommy Hilfiger blazer ($98.50); beaded and pearl necklaces by Sequin ($68 and $148, respectively; 212-398-7363); Joan & David pumps ($200; 800-999-1877)