TTWB: March 2019

Stephanie Winston Wolkoff, on the other hand, isn’t afraid of heights. “The higher, the better!” says the six feet one SWW Creative founder. According to her, it helps to figure out which labels are most consistent when it comes to sizing—she finds the fit of a Rick Owens 41 always works well, whereas Manolos are best at special-order size 43, and Saint Laurent Tribute heels at a solid 42. She recommends pre-ordering larger sizes where possible, which she does with regularity at Blahnik’s midtown boutique. A sensible flat, masculine wingtip just doesn’t appeal—and as she points out, isn’t particularly flattering in a bigger size. Like Williams, she also scours the Internet—Bergdorf Goodman, Neiman Marcus, and Nordstorm all stock up to a 42 online. “I actually have knee problems from years of squeezing into shoes that were too small,” says Williams. “Now I only keep shoes that look and feel great.”