It’s that time of year again when we abandon our strappy sandals and flip flops for heavy duty footwear. The chunky black boot is back with sturdy soles and plenty of buckles. Sam Edelman’s simple ankle boot will protect you from the rain, sleet, or even a polar vortex while Cole Haan offers an elegant riding boot with a techy neoprene back. Alexander Wang’s “Louise” leather motorcycle boots will certainly be the must have shoe among the downtown set, but for ladylike dressing, Ralph Lauren’s “Vallerie” high heeled boots will take you effortlessly from day to night. This season there might be more than one pair of perfect black boots in your future. For 25 kicky options— for every budget— click through the following slideshow.