Baby-Doll Dress

Why It Keeps Coming Back: Ubiquitous in the 60s, the 80s, and even this past season, 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, Valerie Steele of the Museum at the Fashion Institute of Technology. “If you’re not sure it’s right for you, then it probably isn’t.”