Summary List Placement
- Ankle boots are a closet staple that you’ll find yourself reaching for them time after time, especially during colder months.
- A good pair of ankle boots is stylish, multifunctional, snug, and durable.
- We’ve rounded up nine pairs of ankle boots from brands like M.Gemi, Everlane, and Nisolo that deliver classic silhouettes and comfortable fits.
A pair of ankle boots are a wardrobe staple for a reason. They’re timeless in style, versatile, and warm on the feet. Although ankle boots are year-round wardrobe essentials, they work particularly well for completing – and even elevating – fall and winter outfits. Pairing them with jeans and a sweater provides a more casual ensemble for everyday wear while matching them with trousers and a blouse creates a more polished look that could be worn to the office.
And although there are dozens of ankle boot styles out there, the challenging part is finding the perfect pair. Weather, comfort, price, and style are all important factors to consider when selecting a pair that works best for you. To help you get there, we’ve put together a list of ankle boots that span across several brands, fashions, and budgets: Chelsea boots, hiking boots, leather, suede, and beyond. Keep reading for our favorite ankle boot options you’ll want to try this winter.
The best ankle boots in women’s sizes for 2021:
Table of Contents: Static
Updated on 1/13/2022: Updated intro, checked prices and links.
Thursday Boot Co. Downtown Boot
Thursday Boot Co.’s Downtown Boot looks and feels like a premium pair of boots for only $140, plus it offers all-day comfort and a weather-resistant design you can wear in light rain and snow.
Color options: Black Leather, Grey Suede, Sedona Leather
Thursday Boot Co. really considered every detail when they designed the Downtown, from the full glove leather lining that ensures a comfortable fit to the proprietary WeatherSafe suede upper that’s designed to maintain its luster with age.
The boot also has a padded leather footbed that forms to your feet after a few wears for all-day comfort, a grooved outsole that provides better traction and durability, a 1.5-inch block heel that’s reinforced with rubber to give you extra grip, and an unseen zipper and leather pull tab that makes the boot easy to put on and take off.
Product Name: Thursday Boot Co. Downtown Boot
Card Type: small
M.Gemi Corsa Concavo Boot
The M.Gemi Corsa Concavo Boot is comfortable, versatile, and made from buttery-soft leather in artisan Italian workshops.
Color options: Black Croco, Burgundy Croco, Desert Sand Croco, Cognac Leather, Black Leather, Black Leather with Graphic Heel, Grey Suede, Navy Suede, Tan Leopard
M.Gemi is known for making excellent quality footwear, so it’s no wonder the brand is one of our favorite places to find booties. While there are plenty of great options, all of which are handmade in small, family-owned Italian workshops, we’re partial to the Corsa Concavo Boot.
The Corsa Concavo Boot has an elongated shaft, sleek sole, and a small divot in the back of the shaft for a flexible fit. The style, which has a subtle 70s feel, goes with everything and is super comfortable to wear for hours on end. Insider Reviews senior editor Sally Kaplan calls the shoe her perfect pair. The leather and suede iterations are $348, while the croc-embossed leather pairs are a bit pricier at $398. There’s also a tan leopard pair with a calf hair upper that costs $528.
Product Name: M.Gemi The Corsa Concavo
Card Type: small
Everlane Day Boot
The Everlane Day Boot is as effortlessly cool as it is comfortable, and the brand’s refreshing policy on transparency also makes the boot a fantastic choice for those who prefer to buy pieces that are ethically made.
Color options: Black, Ecru, Bone, Brick
Everlane has earned itself a cult following in the last few years, thanks to its modern takes on timeless classics, like jeans and cashmere sweaters, and a refreshing policy of transparency. On its website, Everlane breaks down how much it costs to make all of its clothes, footwear, and accessories (labor, materials, transportation, and duties) and compares its prices with those of traditional retailers. For example, the Day Boot is $225 at Everlane and might be sold for $460 elsewhere.
The Day Boot features a classic Chelsea boot look and is made of 100% Italian leather at a small shoe factory in Brescia, Italy. It’s designed with a 2-inch stacked block heel, cushioned insole, side zipper, and back tabs that make it easy to slip on and off. A few members of the Insider Reviews team tried the boots and found the pairs lasted about a year before suffering from any major scuffing.
Even if you’re not a heel person, that shouldn’t stop you from buying this fashionable boot. The chunky heel is easy to walk in and the cushioned insole gives your feet some extra love. Now you can also get the Glove Boot ReKnit — it boasts the Day Boot silhouette in Everlane’s signature, sustainable ReKnit fabric.
Product Name: Everlane Day Boot
Card Type: small
Blundstone Chelsea Boot
Blundstone has been making boots for 150 years and the Chelsea Boot is an enduring favorite.
Color options: Black, Stout Brown, Navy, Rustic Brown, Rustic Black, Tobacco
I love the look of a heeled bootie, but some days I just want to wear something flat. I recently got a pair of Blundstone Chelsea Boots and they’ve quickly become one of my go-to’s. These boots are seriously comfortable — the footbed is nice and cushioned so they’re easy on your feet, there are two pull tabs to help you slip them on, and there’s also elastic side paneling so they fit you just right.
The materials are really durable; I have friends who have been rocking the same Blundstones for years. These Chelsea Boots definitely have a more casual feel, but that’s one of the great things about them. You can get away with wearing them hiking or for outdoor activities just as much as you could throw them on with jeans or a dress. I even wore these for miles while walking around Amsterdam last winter and didn’t regret a thing.
Product Name: Blundstone Chelsea Boot
Card Type: small
Vagabond Shoemakers Marja Boot
With a pointy cap toe, block heel, and pleated side panels, the Marja Boot from Vagabond Shoemakers is a sleek and comfortable choice.
Color Options: Black Leather
For a boot that feels timeless yet on-trend, look no further than the Marja Boot. The leather side paneling, pointy-toe, and pull tabs all make this otherwise simple silhouette feel really fresh.
The 2-inch block heel adds some height while still being really walkable. Insider Reviews editor Maria Del Russo calls this the perfect pair. “I have gotten these bad boys resoled SO MANY TIMES because I wear them so often,” she says.
Product Name: Vagabond Shoemakers Marja Boot
Card Type: small
Nisolo Classic Chelsea Boot
Nisolo’s Chelsea Boot offers a flattering look and comfortable fit, and it’s ethically handmade and weather-treated in Peru.
Color options: Brown, Black, Brandy, Black/Black
If you’re looking for a black ankle boot that’s perfect for work or the weekend, comfortable to wear, easy to clean and take good care of, and made to last, Nisolo’s Chelsea Boot, seemingly aware of your checklist, is all of the above.
A modern tweak of a classic Chelsea boot, Nisolo’s ankle boot has leather pull tabs for easier putting on and taking off, triangular elastic side panels (instead of standard rectangular ones) for a more unique look and comfortable fit, and a 1.25-inch stacked-leather heel with a rubber heel cap for extra grip and durability.
The Chelsea Boot also has a weather-treated Nubuck leather upper (a more durable type of leather that is resistant to everyday wear and tear), leather sole, leather lining, and soft leather insole, and it is handmade at an ethical factory in Peru. It’s not a cheap boot at $200, but thankfully everything about it is premium and ethical — and it is indeed very comfortable to wear all day once you properly break it in.
Product Name: Nisolo Chelsea Boot
Card Type: small
Marc Fisher LTD Yale Chelsea Boot
The Marc Fisher LTD Yale Chelsea Boot‘s pointy toe is a “really love it or really don’t” style that is sure to be a standout amid a sea of black ankle boots.
Color options: Black Croc Leather, Black Leather, Black/White Snake Print, Cream Leather, Cloud Suede, Dark Grey Snake Print, Natural Multi Snake Print, Rhum Suede, Tan Leather, Tan/Black Leather
It’s rare for over 90% of Nordstrom reviewers to agree on something, but it appears that the Yale Chelsea Boot is a black ankle boot that they collectively agree is awesome, for a number of reasons. Petite women love the boot’s pointy toe since it effortlessly elongates their shorter frames while women in search of that perfect blend of comfort and style love its low 1.5-inch heel, soft leather, and non-existent break-in period. After putting it to the test, it’s clear to me, too, that there’s a lot to love about this fun little ankle boot.
With 10 different colors and patterns to choose from, you can be sure you’ll find a style you love.
Product Name: Marc Fisher LTD Yale Chelsea Boot
Card Type: small
Asos Design Action Chelsea Boot
The Asos Design Action Chelsea Boots are on-trend and affordable enough that you can replace them every few seasons.
Color options: Black
It can be hard to find nice boots for less than $100, so at $48, the Asos Design Action Chelsea Boots are especially affordable. The upper is made of faux leather, but it looks just like the real deal. The ribbed side paneling makes them easy to slip on and off, and it also adds some intrigue to the otherwise simple silhouette.
Asos is always releasing new iterations of the classic Chelsea boot, but right now this one with the chunky lug sole is even more of-the-moment. It also adds just a bit of height while still being walkable. This is a casual pair that you could wear with literally everything, from joggers to dresses.
Sam Edelman Packer Bootie
The low-profile, chunky-heeled Packer Bootie from Sam Edelman is a favorite year after year, yet the look always feels fresh.
Color options: Asphalt Suede, Black Leather, Deep Saddle Leather, Putty Leather
If you like a true ankle bootie with a lower profile, you’ll love the Sam Edelman Packer Bootie. The 1.5-inch chunky heel is easy to walk in, even if you’re not great with heels. There’s also a functional side zipper that makes putting the shoes on easier and faster.
The color options are all great neutrals that go with pretty much anything, depending on what colors you find most in your wardrobe. And, the style isn’t too trendy, so you know you can wear this bootie for seasons to come.
Check out more of our style guides
Whether you’re wearing them to go on a run or just lounge around the house, everyone needs a nice pair of leggings. We love the ADAY Throw it Higher Leggings because not only are they incredibly comfortable, but they have zip pockets to hold all your belongings.
A cozy cashmere sweater can be really expensive, but we’ve found lots of great ones for $100 to $300. Everlane is our favorite place to buy cashmere sweaters because they’re no-frills, but high quality. At just $100 and with a range of color options, it’s a closet staple.