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 ($14, 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."
2 of 10Chris Bartlett
Why it keeps coming back: Ubiquitous in the 60s, the 80s, and even just recently, the Empire-waisted wonder “always returns because it’s very forgiving,” says Rebecca Taylor, a fashion designer in New York City. “People from thin to not-so-thin can wear these dresses, so no one wants to part with them,” says Nicole Miller, a fashion designer in New York City.
Keep it if: It is made from a long-wearing fabric, like silk or wool, and has a trapeze or A-line shape―“but no more voluminous than that,” says Finney. The most recent iteration was positively billowing, bordering on maternity gear, and it probably won’t be trendy again. Instead, store the subtler shapes that gradually flare away from the body.
Toss it if: The color (like an over-the-top hot pink), embellishments (ruffles and rosettes), or length (Shirley Temple–short) make it too youthful looking. “The age limit on looking good in this style is lower than you’d think,” says Steele. “If you’re not sure it’s right for you, then it probably isn’t.”
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Platform Shoes and Boots
Why they keep coming back: Platforms have made a footprint on almost every decade of the last century―arguably no more so than in the 70s, when they graced the feet of Stevie Nicks wannabes and hustled the night away under disco balls. “For a heel, they’re easy to walk in, and they have a slightly funky edge,” says Finney. Adds Trina Turk, a fashion designer in Los Angeles, “Hey, it’s a powerful feeling to be taller!”
Keep them if: The shoe is sophisticated (you don’t want to look like a mall-prowling teen) and at least somewhat practical. “A four-inch heel and a one-inch front platform is the max,” says Nicole Miller. Any higher will look a little RuPaul―and be tough to walk in.
Toss them if: “Anything about them is too extreme―like design, material, or thickness of heel,” says Carson Kressley, the host of Lifetime’s How to Look Good Naked. In that case, what goes around definitely won’t be coming around again.
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Why it keeps coming back: This floaty, feminine style has been a favorite of Summer of Love hippies, carpooling moms, and everyone in between. Who doesn’t groove on an elastic waistband?
Keep it if: “It’s unique looking, interesting, or hard to find―anything very ethnic, printed, or embellished, for example,” says Verdi. Adds Rebecca Taylor, “Eyelet peasant skirts always look fresh.”
Toss it if: “It’s a bright color or neon,” says Kressley. Most likely, those skirts won’t come back; and if they do, you should be able to pick up a new one at low cost. Also, anything that’s overly costumey―making you look like an extra in Pirates of the Caribbean―has got to go.
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Why it keeps coming back: “It’s a way to communicate sexy femininity without being revealing,” says Trina Turk. Which is why power dressers from the hard-charging Gordon Gekko 80s to today have tied up deals in them.
Keep it if: “It’s well made by a big-name designer, because they tend to use better proportions. Or if it’s dramatic, with an extra-long tie, so it is a statement piece, not just that season’s fad,” says Verdi.
Toss it if: It’s a cheapo, mass-produced take on the look, in which case it’s bound to bear signs of its era (a too-boxy cut or a synthetic material that won’t age well). And, says Taylor, “get rid of anything that’s too reminiscent of Tootsie.”
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Leggings and Skinny Jeans
Why they keep coming back: Ultra-fitted bottoms―veterans of Debbie Harry’s style era and Debbie Gibson’s, too―are a recurrent trend for a reason. “Skinny jeans can be dressed up or down,” says Charles Malka, the founder of the Charles David line of shoes and accessories, while “leggings are a great way to show off your legs without showing skin―and perfect for layering in the winter,” points out Taylor.
Keep them if: You’ve invested in high-quality leggings, “because they’re charging more for them each time around!” says Valerie Steele. Any pairs in dark colors and free of lacy trim are worth stashing; they can stand in for tights during times when leggings are not au courant. As for skinny jeans, keep yours if they’re figure-flattering and made from “a pure, classic denim,” says Verdi.
Toss them if: Era-specific details―such as a distinctive wash, zippers at the ankles, or prominent embroidery―decorate the denim. “And get rid of any leggings in bright, all-the-rage colors or patterns―they’re not going to work again,” advises Kathryn Finney.
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Why they keep coming back: Said to have been inspired by the footwear of 19th-century soldiers, ankle boots are “easy for women of all calf sizes to wear―and you can get the look and the height of a boot without having to go full-length under trousers,” says Robert Verdi.
Keep them if: They’re “made from fine leather in classic colors, like black, brown, and dark blue,” says Finney, and any necessary rehabbing can be done easily at a shoe-repair shop.
Toss them if: They have an obvious faux finish, like lizard, which can make the boots seem cheap, or if “the toes are too pointy, which makes your feet look a bit funny,” says Charles Malka. And retire boots with studs, fold-over flaps, or other touches that scream of-the-moment fashion.
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Why it keeps coming back: Since its invention in the early 1800s, the high-gloss finish has been hot (think Jazz Age Mary Janes and swingin’-60s go-go boots), not, and then hot again―repeatedly. “Patent leather gives your outfit an instant wow factor, but it’s still an approachable and wearable trend,” says Verdi.
Keep it if: It’s an accessory in a timeless style, such as a clutch or a simple handbag, skinny belt, or pumps, “especially in a basic color that will always resurface, like black, nude, red, or Bordeaux,” says Malka. Also a keeper: a patent trench coat with a classic cut.
Toss it if: It’s used in conjunction with another fad, like “a shiny shrunken jacket with shoulder pads,” says Kressley. “Joan Collins gave hers away, and you should, too.” The odds that two trends are going to be popular again at the same time are slim to none.
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Why they keep coming back: Generations of high-stepping women have loved these shoes since Italian designer Salvatore Ferragamo crafted the first pair from wine-bottle corks in the 1930s. “Wedges give women the psychological feeling of great height―but with much more comfort than typical heels,” explains Verdi.
Keep them if: They’re in pristine condition. Wedges are often made from materials―like cork, natural sisal, or Lucite―that are vulnerable to wear and tear. “This trend comes back in almost exactly the same way, so hang on to the ones that have that vintage look,” says Kressley.
Toss them if: “They don’t have an open toe; closed-toe wedges tend to be uncomfortable, and you’re never going to want to wear them again,” warns Nicole Miller. Says Charles Malka, “Chuck the winter ones, too. This is a style mostly worn in the summer.”
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Why they keep coming back: "Animal prints play off the idea of women being vixenish, wild, and fierce," says Steele. So it's no surprise that fashionistas have been spotted in the prints since the cave-dwelling days―though the trend is most strongly identified with the 50s and 60s, when it was favored by sultry pinup girls, like Bettie Paige and Ann-Margret.
Keep them if: The pattern is in the "large cat" family (cheetah and leopard prints) or black-and-white zebra zigzags, which have the most staying power. Accessories like handbags, belts, and ballet flats hold up well, as do blouses and basic sweaters, like cardigans and V-necks. And stow coats and dresses with enduring silhouettes, such as wrap and A-line designs.
Toss them if: "The print is really bold―giraffe or spotted pony―or in unnatural colors, like lime green or pink," says Kressley. Also ditch larger-than-life patterns that aren't true to scale.