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.”