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.”