These 17 Stiletto Ankle Boots Go With Everything

For most of us, winter means trudging through snow and ice in our sturdiest winter boots. However, as practical as those may be, they aren’t always the most stylish. We’re not ones to sacrifice our safety for style, but in those moments when you aren’t trekking from place to place, give yourself a boost—literally and figuratively—with a pair of stiletto ankle boots.

As tempting as it may be to reach for your block heels or combat boots this season, sleek stiletto booties will give your ensemble an unparalleled level of chic. Whether you dress up a casual sweater with jeans or amp up a sophisticated office look, this ankle boot style is guaranteed to go with anything you wear (we promise!). Ahead, check out some of our favorite versions of this classic ankle boot style.