During the colder months, ankle boots look amazing with jeans, or a skirt or dress with tights. During warmer months, you can get away with wearing the right pair of ankle boots with shorts or a dress. There are so many fun ones out there: wedge, heel, flat, cut-out, laced, buckled, and the list could go on. And they’re so big for fall — you really should own a pair. Ankle boots are the latte of footwear: They’re sophisticated, great any time of year, and an all-around crowd-pleaser. In fact, we’re fairly sure, if we were forced to play favorites with our footwear, it’s booties that would take top spot.