If you are itching to rock high-tops like cool-girls Gwen Stefani and Drew Barrymoore but worried about how to style them—fear no more! We asked Holli Rogers of Net-a-porter.com for tips on how to chic-tify these retro (and super comfy!) kicks. “Wear them with a boyfriend blazer, skinny cigarette pants or jeans and a vibrant tank for a downtown look. If you prefer wearing dresses, an A-line hemline that falls above the knee looks best,” she said.

Clockwise from top: Pierre Hardy, $430; call 949-642-4423, Converse, $65; visit converse.com, Lanvin, $595; visit net-a-porter.com, Creative Recreation, $95; visit shopcreativerec.com, Keds, $65; visit keds.com.