It's a year round staple for most but if you are like me and opt for free toes as often as possible, fall and winter might be the only time you boot up. Rather than jump in feet first, I tend to go slowly. Ankle boots are the perfect way to begin the transition from sandals to cold weather staples. These are a few of my favorites in black. Clockwise: Glitter, wedge, clog, leather and suede mix.