The 15 best ankle boots for winter and beyond

Thursday Boot Co.'s Downtown Boot looks and feels like a luxury pair of boots, featuring insoles for all-day comfort and a weather-resistant design you can wear in light rain and snow. 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 texture with age. 

The boot also has a padded leather footbed that forms to your feet, 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 a disguised zipper that makes the boot easy to put on and take off.

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. The M. Gemi Liana Boot is comfortable, versatile, and made from buttery-soft leather. The boot has an elongated shaft, a rugged sole, and a panel of leather-covered elastic for a flexible fit. It comes in two colors, black and ecru. 

All of M.Gemi's shoes are handmade in small, family-owned Italian workshops, and after testing several of their shoes (including the famous Felize moccasin), we have never been disappointed by their quality.

Revolve is always our go-to for trendy styles, and its shoes are no exception. This pair from Jeffrey Campbell is giving Chanel-meets-YSL vibes, but without the designer price tag. 

The pointed patent toe is sleek and chic while the matte black upper adds an edgy contrast. It's a simple yet fun twist on the classic black stiletto bootie, perfect for date night. 

Blundstone has been making boots for 150 years and the Chelsea Boot is an enduring favorite. 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-tos. 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. 

These Chelsea Boots definitely have a more casual feel, but that's what makes them great for hiking or other outdoor activities. I even wore these for miles while walking around Amsterdam last winter and didn't regret a thing.

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 2-inch block-heel style and is made of 100% Italian leather at a small shoe factory in Brescia, Italy. They have cushioned insoles, side zippers, and back tabs that make them easy to slip on and off. A few members of the Insider Reviews team tried the boots and found that the pairs only started showing real signs of wear about a year into heavy-duty use.

It can be hard to find nice boots for less than $100, but the River Island Side Zip Ankle Boots are the perfect combo of affordable, chic, and trendy. The upper is made of faux leather, but it looks just like the real deal. The gold detailing on both the heel and the zipper also make it easy to dress up a pair of jeans or a little black dress.

If you're looking for a gray ankle boot that's perfect for work or weekends, comfortable to wear, easy to clean, and made to last, Nisolo's Chelsea Boot (seemingly aware of your checklist) is all of the above. It's not a cheap boot at $200, but its top quality materials and commitment to ethical production help justify the cost. Plus, this pair is extremely comfortable to wear all day once you properly break it in.

A modern tweak of a classic Chelsea boot, Nisolo's ankle boot has leather pull tabs to make it easier to get them on and off, along with triangular elastic side panels (instead of standard rectangular ones) for a more unique look and comfortable fit. The stacked-leather heel is low at just over an inch, with a rubber heel cap for extra grip and durability.

The chunky heeled Sidney Ankle Bootie is a boot that's just as comfortable as it is sturdy. With an upper part sock and part leather, the Sidney Ankle Bootie is the perfect balance of comfort and durability. Its boot shaft stands at 3.9 inches allowing the wearer to stay afloat any element the cold weather brings. Whether you get brown, black or eggshell, the buckle detailing and line stitching work together to make choosing between the three shades very difficult.

With a pointy cap toe, block heel, and pleated side panels, the Marja Boot from Vagabond Shoemakers is a sleek and comfortable choice. The detailing makes this otherwise simple silhouette feel fresh and elegant. 

The two-inch block heel adds some height while still being really walkable. Former Insider Reviews editor Maria Del Russo calls this the perfect pair of ankle boots. "I have gotten these bad boys resoled SO MANY TIMES because I wear them so often," she says.

Everlane's sock-like Glove Boot is so comfortable it's almost hard to fathom. The upper is made from 88% recycled polyester with just enough stretch to feel flexible but not flimsy. The heel is low so they're super walkable for long days out and about, but the black pair in particular looks most elegant and is virtually indistinguishable from a leather boot until you get up close. Folks on our team have been wearing these since they first launched years ago and we still stand by them! 

With its heart-shaped hardware and Milled Nappa leather on a roughly two-inch platform sole, the Devon Heart Leather Platform Boots blurs the line between soft and rugged. Known for their tough construction, Dr. Martens are durable and heat-sealed. While most of their boots take doubling up on socks to break them in, this bootie is comfy and can easily be worn brand new.

Insider Reviews' executive editor Sally Kaplan deems these Blundstones the ultimate ankle boots for fall and winter. "They have a shearling insole that keeps my feet warm and toasty, and a waterproof construction that makes it safe for me to step in puddles or snowy slush," she says. The rugged sole has excellent traction, while the signature pull-tab makes it easy to get the boots on and off. An elastic panel ensures enough flexibility and comfort around the ankle that Sally has even worn these hiking along rocky trails with zero discomfort. 

If you prefer to wear these with thick socks, you should go up a half size. Otherwise, they run true to size.

The Tara Chelsea Boot is a comfy bootie that can be styled with just about anything. "After eyeing these Vagabond boots for a few years I finally purchased them last fall," Insider Reviews associate story producer Elena Matarazzo says. "They have exceeded my very high expectations and look perfect with my vintage Levi's, trousers, and slip skirt." Like a Doc Marten, they add height and dimension to any outfit and like a Blundstone, they don't compromise comfort to do it.

The low-profile, chunky-heeled Packer Bootie from Sam Edelman is a favorite year after year, yet the look always feels fresh. If you like a true ankle bootie with a lower profile, you'll love the Sam Edelman Packer Bootie. The one-and-a-half-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.

It's rare for over 90% of Nordstrom reviewers to agree on something, but the Yale Chelsea Boot has won the hearts and minds of many a Nordstrom shopper, as well as our former editor-in-chief, Ellen Hoffman. These have been her go-to boots for several years in a row, and she swore they were the most comfortable ankle boots ever. 

She and other petite folks love the boot's pointy toe since it effortlessly elongates shorter frames, and appreciate its low heel, soft leather, and non-existent break-in period. After putting it to the test, it's clear that there's a lot to love about this little boot, which runs true to size and comes in several other neutral suedes.

• The best white T-shirts for women
• The best leggings
• The best cashmere sweaters