The best ankle boots are the ones that capture the fashion zeitgeist yet serve all the qualities of a longstanding classic in your wardrobe. You really can have it all—when it comes to shoes, at least—and this winter, there are countless covetable styles to choose from.
Tasha Tilberg can’t believe that 1996 was more than 25 years ago. As I flaunt her former FASHION cover, she can’t help but laugh affectionately. “I remember feeling so grown-up when we shot this,” she says warmly over the phone from her home