Leather Bomber Jacket

Why It Keeps Coming Back: Strictly for the cockpit set when it debuted during World War II, the bomber jacket, which saw plenty of action on terra firma after it caught on with 80s-era trendsetters, like Madonna, is “chic and a little tough at the same time,” explains Valerie Steele, director and chief curator of the Museum at the Fashion Institute of Technology, in New York City.

Keep It If: The cut flatters you and the style sticks as close to the original as possible, as any major variations tend to look passé. Take stock of the cuffs, too: “Leather cuffs are more classic than the ones with the knit ribbing,” says Kathryn Finney, author of How to Be a Budget Fashionista (Ballantine Books, $13, www.amazon.com).

Toss It If: It’s exaggerated in any way. “No tight sleeves, loose bodies, or belts,” cautions Robert Verdi, a fashion stylist based in New York City. “And if it’s red with an embroidered eight ball on the back, ditch it.”