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.