10. A chunky ankle boot that should really start negotiating for PTO now, considering you'll likely wear them every darn day.

Perhaps best known for over-the-knee boots, Stuart Weitzman's selection of ankle and mid-length styles shouldn't be ignored. Here, a classic silhouette gets a chic update with a wrapped design and ...

A trusty pair of ankle boots ... make Everlane's Day Boot right on trend, while soft Nappa leather and slender seams give the style timeless appeal. Snag them in practical black or brown or ...

The classic Docs are the ankle-length lace-up black boots, complete with their iconic yellow stitching in the sole and the little flap on the back, a helpful addition when pulling the boots on ...

The ankle-length boots also feature a neat zip fastening with gold hardware detailing to provide an "upper class look", according to reviews. Available in two autumnal shades - black and brown ...

That's why when I stumbled upon the Superga 798 Rubber Boots Mid – now with a tempting 20% discount - they seemed like the perfect choice. The ankle length ... I chose the black pair, you ...

If you’d like a shorter design for winter, look no further. We loved Aeyde’s ’90s-leaning black leather ankle boots, as well as Dear Frances’s Cade, which provides a more sturdy step.

11. A chunky ankle boot that should really start negotiating for PTO now, considering you'll likely wear them every darn day.