I've been seeing short black booties on Michigan girls about town lately and they can look fabulous with the right pairing. Ankle boots seem far more intimidating to wear for the first time than they actually are. For beginners, they don't have to be worn with bare legs like Mischa here. The best way to ease into wearing them is to pair with a chic skirt and black tights (far right). Wearing black ankle booties with black tights can make your legs appear super long, promise! Grey tights will do the trick as well. Booties, as with most fashion choices, can be purchased at high prices in most department stores. I searched around to find equally bold and trendy booties for much less than at most department stores. From left to right, Kenneth Cole at Piperlime for $50, Zappos for $64, and Target for $29.99.