Ask a Cool Person Where we ask stylish individuals with particular, exacting, or simply exceptional taste to tell us about the things they’re actually buying. Read more here . Photo: Photo: Jo Rosenthal In this article Under $250 Under $500 $500 and over Throw on a knee-high boot, and it instantly elevates a plain skirt or dress into a full-on outfit. Finding the right pair can be a bit difficult, though. “Tall boots open up more room for mistakes, flaws, and ill-fitting issues,” says stylist