Long leather gloves. “They look so chic, and they’re a great way to stretch out your autumn outerwear [into winter],” says Krentcil. Check out Marc Jacobs and Prada, which first popularized them.

Wide-leg jeans. The reign of tight, low-rider jeans is finally over. Look for denim that rides higher and has more room in the leg. And wear them with a heel. “A little elevation goes a long way,” says Krentcil. “Otherwise, you could look stumpy.” Try Made in Heaven, sold at Intermix stores, or Grey Ant jeans ($253 to $330) at shopbop.com.

Plastic accessories. Look for colorful plastic rings ($35) at madeher think.com. “But don’t overdo it,” says Krentcil.

Colored tights. Wear blue or purple with a black dress. And don’t be afraid to pair them with open-toed shoes—yet another great way to move your warm-weather items into winter.