DO wear ankle boots with longer skirts. They look best with of-the-moment hemlines—midi skirts and pencil skirts that fall at (or below) the knee are great options.
DO opt for basic black booties that hit at the slimmest part of your ankle, especially if you’re self-conscious about your legs. The same way nude pumps make calves look long and lean, black ankle boots worn with opaque black tights have an elongating effect (not to mention it’s a classic and office-appropriate combination).
DON’T pair a skirt or dress with flat booties. It will make your legs look shorter than they are.