The Best Ankle Boots for Work: Stylish, Comfortable, Weatherproof & More!

Sure, we all know what wardrobe essentials for work professional women are supposed to have in their closets, but if you’re buying one for the first time or replacing one you’ve worn into the ground, it can be a pain to find exactly the right incarnation in stores. In “The Hunt,” we search the stores for a basic item that every woman should have. Today's hunt: the best ankle boots for work.

Readers, which ankle boots are you loving this winter? Which boots (in general) are you wearing most often?

Ankle boots sit in an awkward middle ground in the professional wardrobe. Too casual and they read weekend; too sleek and they veer into evening. Heel height, shaft width, toe shape, pant length — every small detail seems to matter more than it should, especially if you want a pair that works with both trousers and skirts. And that’s before you factor in weather, walking, or the reality that many of us want fewer shoes that do more jobs.

{related: The Ultimate Guide to Business Casual for Women}

Editor's Picks: Our Latest Favorite Ankle Boots for WOrk

Hunting for ankle boots and booties? As of 2026, some of our top picks for work include these… Also check comfort brands like Dansko and Paul Green.

The Best Ankle Boots for Work

A Walkable but Sleek Bootie: J.Crew

I've liked J.Crew's kitten-heeled boots since they came out a year or two ago, but these newer boots with a block heel look a lot more walkable.

They come in four colors, and are $298 at full price — but they're currently on a 40% off sale. Nice!

You can find a similar, budget-friendl(ier) option at Quince.

A STylish Flat Boot: STaud

I've liked the heeled versions of these extremely popular Staud boots for a while, but I haven't seen this flat version of the boot — love! I like the squared toe. It comes in a number of colors and ranges from $395-$450; there's also a knee high flat boot.

You can find similar options at Jenni Kayne or Aeyde (with a slightly taller heel).

A Comfortable Kitten Heeled Boot: Marc Fisher LTD

Readers have always liked Marc Fisher shoes — the brand made everyone's favorite Chelsea boot and block heel pump, after all. They have a number of kitten heel boots right now that are getting great reviews.

Looking for something similar? J.Crew, Staud, Sézane, and Madewell have similar options.

An Affordable Waterproof Ankle Boot: Blondo

Blondo is known for having comfortable, affordable, weatherproof shoes — and they often have a BUNCH of options. This boot is getting great reviews at Nordstrom! It was $180 new, but is now marked 50% off.

A Washable Fabric Ankle Boot: Rothy's

Rothy's just started selling low heels, including these boots, and I like them. They're made from a water-resistant merino, and feature the brand's innovative insole that readers love with flats. The merino wool is RWS certified, for a bit of an eco-friendly boost.

The boots are available in sizes 5-13 for $269. You can find similar fabric options from Vivaia, Everlane, and Quince.

A Stylish Weatherproof Ankle Boot: Aquatalia

A Classic Chelsea ankle boot: Marc Fisher LTD

These Marc Fisher LTD ankle boots are best-sellers and reader favorites. It's come in a bunch of colors and materials over the years.

Another old favorite that's still around: this Chelsea boot from Sam Edelman.

Other Boots for Work Outfits

The Best Sleek But Walkable Boots for Work

Our favorite sleek but walkable boots for 2026 include the following… also check out comfort brands like Naot, Paul Green, Rothy's, and Dansko.

The Best Weatherproof Shoes For Your Commute

Hunting for weatherproof shoes for work? As of 2026, our favorites include brands like Blondo, La Canadienne, and Aquatalia — also check out waterproof sneakers like Allbirds.

The Best High-Heeled Boots in General

As of 2026, knee-high boots with a heel are back! Some of the best-looking options include these from J.Crew, Schutz, Veronica Beard, Staud, and Stuart Weitzman. If you're looking for an affordable alternative to try the style, check out these boots at DSW or these at Amazon, both under $100.

The Best Knee-High Boots for Work

Hunting for flat knee-high boots? Some of our long-standing favorites (as of 2026) include La Canadienne, Stuart Weitzman, Sam Edelman, and Sofft; also check this Cole Haan option, this Teva boot (!), and Vivaia for comfort (and tons of color options).

Like this feature? Check out other recent installments!

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