29 Fresh Takes On The Little Black Boot

Choosing between a classic and a trendy piece in regard to any wardrobe addition is not an easy decision. A staple, while reliable, can sometimes feel tiresome while that trend-driven item might not be worth the investment if it's only good for one season. The solution is all about the subtle merging of tried-and-true silhouettes and unexpected embellishments to get a little bit of both. And when it comes to the iconic black ankle boot, that means opting for new heel shapes, inventive designs, and subtle spins on the classic.

These cool takes on an old reliable can make your go-to shoe feel totally fresh. Because like it or not, bootie season is here — and if you're ready to ward off the upcoming chill in style, these boots have you covered...or, well, at least your toes.