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.