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

Whether you're more of a black ankle boots kinda person ... The Chelsea style is a classic boot fave and we love the taller ankle length. Have you spotted a more perfect western boot?

To offset the casual feel of ankle-high boots, try wearing them ... Start with a pair of black leggings as your base, add a turtleneck and tunic-length sweater in similar tones, and finish the ...

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 ...

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 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 ...

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.

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