Thanks for signing up!
Access your favorite topics in a personalized feed while you're on the go.
I've tested over 40 pairs of ankle boots to find the best and comfiest ones
When you buy through our links, Business Insider may earn an affiliate commission. Learn more
Along with a pair of nude pumps and classic white sneakers, a trusty pair of ankle boots is a must-have in any wardrobe. Their versatility is almost unmatched: not only can they transition from brisk fall well into warmer spring days, but they also look equally chic with jeans and leggings as they do with skirts and dresses.
But let's face it: not all ankle boots are worth your investment. The best ankle boots are just as comfortable and durable as they are stylish. Ahead, we rounded up a handful of styles that check both boxes — from winter-ready waterproof options and everyday Chelsea styles to splurge-worthy suede booties.
If you're in the market for boots with a taller shaft, see our piece on the best knee-high boots.
Advertisement
A quick look at 5 of our favorite ankle boots
Everlane's Day Boot is a buttery soft, true to size, walkable closet staple that's perfect for everyday wear. It's one of our favorite shoes from the brand, even after testing nearly every pair Everlane has made in recent years.
Winter is no match for these waterproof and warm Chelsea boots. Blundstone paired their classic aesthetic with a sheepskin footbed that is a godsend when it's freezing outside. Plus, they sell versions without the lining if you live in a milder climate.
These stretchy boots from Vivaia are exceedingly comfortable, water-repellent, and made of an elastic outer that can accommodate wide feet. We love how easy they are to slip on and how you can splash through puddles with no stress.
At under $40, these ankle boots from Amazon are a bargain hunter's dream. They're a great classic style that you'll find yourself reaching for every time the weather gets a little chilly. Plus, they have a whopping four-and-a-half stars and nearly six thousand reviews.
These four-inch heeled boots are more comfortable than some sneakers. In fact, I can literally run in these beautifully crafted shoes. Plus, the Pilar is the ultimate fall boot with its chunky silhouette and suede colorways.
An angled block heel and square toe 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 in seasonal suede colors that pair beautifully with fall and winter outfits alike.
"Since getting Everlane's Day Boot in Burgundy I've worn them to the office, out on the weekends, to trek my typical hour-plus of walking along unforgiving sidewalks, and stood in them for a three-hour concert after wearing them at work all day. I won't pretend that they're the same as tennis shoes, but they're incredibly comfortable for boots. The low heel is indeed walkable, and the cushioned insole does its job well," says Mara Leighton, former style editor for Insider Reviews.
See our full Everlane Day Boot review for more reasons why we love it so much.
These best-selling ankle boots have garnered thousands of five-star reviews, and it's easy to see why: with a flexible non-slip sole and memory foam padded insole, they're remarkably comfy. Not to mention, they look effortlessly put together, thanks in part to the stacked Cuban heel, grosgrain piping, and almond-shaped toe.
These booties come in an array of neutral colors — like taupe and cognac suede and timeless black leather. Reviewers say it only takes about a day to break them in. If you're between sizes, though, they recommend sizing up.
These Chelsea-inspired ankle boots feature a sturdy block heel, stylish pointed toe, and side stretch gore for extra flexibility while you walk. Even though the heel is 2.75 inches, it feels closer to 2 inches — due no doubt in part to the cushioned footbed with arch support.
My wardrobe is probably 75% black, and I love how the graphite pair of Demmi's can help to break up an otherwise monochromatic outfit while still maintaining a chic neutral palette.
Did I mention they're made with leather responsibly sourced through Leather Working Group-audited factories? That means the tanneries the materials came from meet higher social and/or environmental standards.
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.
When style editor Samantha Crozier tested out the Pilar for her Inez review, she assumed she'd barely be able to walk in the 4-inch heels. Thanks to the padded footbed, shallow pitch, and elastic side panels, however, she walked a mile and a half with no foot pain whatsoever.
"Despite how fashionably unstable they may look, I could easily stand on the crowded, bumpy NYC subway without being terrified of toppling over — which is a true test of balance," she says.
If you're in the market for the best platform ankle boots, these should absolutely be your choice.
Amazon is always a great place to find a deal, and these boots are no exception. Here's what I said about them in my guide to the most comfortable boots for women:
"Buying budget-friendly footwear on Amazon really is a crapshoot — sometimes what I get looks hilariously nothing like what I ordered. But every once in a while I get lucky, like I did with this pair of platform wedge booties. Even though they're made with faux suede, they look like they could easily cost twice what I paid for them."
Functional features like a lug sole mean that you can wear these even on days when it's a little wet out. But if you want to wear them well into the winter, we suggest investing in a water-proofing spray.
The sock boot trend is definitely still in full swing — and this modern square-toe pair is just as eye-catching as it is comfy. What sets the VIVAIA Regina Pro apart is not just the anti-slip outsole and pressure-relief herbal insole, but also the water-repellant upper that stretches to accommodate even the widest feet.
"These boots are incredibly comfortable. The cloth material makes them super easy to slip on in the morning — plus, they're kind of reminiscent of Balenciaga's famous sock boots. But unlike Balenciaga boots, these are incredibly practical and sold at a great price point. I've worn these in a drizzle and have been impressed with the water-repellent feature, but I would avoid wearing them in a downpour. Plus, how cute is the red heel on a black boot?" — Samantha Crozier, style and beauty editor, Insider Reviews
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.
You might expect these sky-high suede booties to feel pretty unstable — not to mention uncomfortable — but that couldn't be farther from the truth. Sure they're pricey. But if your budget allows, style editor Samantha Crozier insists they're worth the splurge: after all, they come from the same factory that crafts Jimmy Choos.
"Scarlett Chase's motto is 'shoes designed for wearing' and these are immensely wearable. They absolutely don't look it — but they literally feel like sneakers. Inside, there's a brilliantly designed arch support system that cradles your feet with padding.
"I'm a heel enthusiast and literally wrote the guide to the most comfortable heels by testing dozens upon dozens of shoes. In my professional opinion, these get a standing ovation. I've worn them for hours and hours with no pain, which is a huge feat for three-inch booties without a block heel or platform." —Samantha Crozier, style & beauty editor, Insider Reviews
In case you weren't aware, this ultra-short take on UGG's iconic sheepskin boots sold out several times last year — which might have something to do with the fact that a number of celebs, including Keke Palmer, Kylie Jenner and Gigi Hadid made them cool again.
I can confirm that they live up to the hype. Whether I'm slipping these on with leggings or jeans, I know my feet will always thank me — particularly on those notoriously frigid New England days. They're made with the same signature luxe suede and ultra-plush upcycled wool-blend lining as the original, but the shorter shaft and 2-inch platform give them a sleeker look without sacrificing practicality whatsoever.
Also worth mentioning: These booties are crafted with responsible materials that allow the company to reduce dependency on fossil fuels.
Read our full Ultra-Mini Ugg Boots review.
We love Vivaia, as evidenced by the fact that there are multiple picks from the comfort-focused brand on this list. But while most of its offerings tend toward functionality rather than high-fashion, these kitten-heeled boots are among its most elegant shoes.
"An ankle bootie like the Alexandra has the perfect heel for people who hate wearing heels. The kitten stiletto looks like it'd be precarious to walk in, but I promise it's not.
"It curves around the heel cups to support your ankles, and has a flared base that steadies you across whatever surface you're stepping on. Inside are densely padded footbeds that feel like a soft quilt. The stretchy shaft also negates any friction around the skin, so they're easy to break in." —Gabrielle Chase, associate style editor, Insider Reviews.
For more of our favorite picks from the brand, see our full Vivaia review.
Lace-up boots are synonymous with the Dr. Martens brand — but the beauty of this specific style is that it's convertible. While you can lace them up, they also come with a removable zipper detail as well. In other words, it's two shoes in one.
Whether you opt to lace or zip them up, these ankle boots add some edge to feminine dresses and skirts, while also pairing perfectly with straight-leg, skinny, and boot-cut jeans. Reviewers strongly recommend opting for a half size down, unless you have especially wide feet.
For guidance on sizing and breaking them in, read our full Dr. Martens boots review.
"Margaux shoes can be hit or miss for pretty much everyone on our team, but these boots are a definite win.
"Off the bat, it's important to note that Margaux's sizing can be a little finicky. My feet are not particularly wide, but I always opt for a wide fit from the brand because their regular width is very narrow. In the right width, these boots fit like a glove.
"The cushion and arch support makes them so walkable; they were the only shoes I brought for a 10-day Europe trip in December and my feet survived so many 14-hour walking days in the cold and the rain. I love the little bit of western flair and the stretch panel on the side that keeps them from digging into your calf.
"Besides tricky sizing, the only frustration I had with these boots was that the finish on the sole had some peeling, but that hasn't taken away from how much I love wearing them when chilly weather rolls around." —Sally Kaplan, executive editor, Insider Reviews.
"What can I say about these except that they're another hit by one of my favorite brands ever for comfortable, stylish shoes? I've reviewed Inez and raved about almost all their footwear. This one is no exception.
"It is made of soft, flexible leather. The footbed is secure and soft. Plus, it is exceedingly walkable — even when you don't account for the fact that the heel is over three inches high. But if that seems like a little too much elevation for you, you can check out the slightly shorter Paz 70.
"Where Inez really shines above all else is their craftsmanship when it comes to heeled shoes. Each one is better than the next and you can't go wrong with their boot selection." —Samantha Crozier, style editor, Insider Reviews.
Combat-esque boots have been everywhere in recent years, and this Sam Edelman pair is just edgy enough to give any outfit some much-desired attitude. I love that the chunky lug sole is sturdy enough for me to tread through some light snow, but they also look polished enough to wear to a brunch or coffee date. The padding around the ankles adds to the comfort factor, and since they have a 1.4-inch platform, I get a boost without feeling like I'm wearing heels.
I own the dark cashew color — which I like pairing with black maxi dresses and faux leather leggings — but you can't go wrong with any of the other luxe neutral shades, some of which feature contrasting detailing.
What's not to love about a wedge bootie? Since they distribute your weight more evenly across your foot, they offer a little more stability and comfort while still looking polished enough for a night out. The fashion-forward Teeray ankle boot by Vince Camuto boasts a sophisticated pointy toe, side zipper, and padded footbed. They're true to size, and trust me: you'd never know from wearing them that the heel height is 3.4 inches.
I have a pair in the statement-making swan croco color, which never fails to liven up a basic ensemble. That said, they also come in timeless black leather and tan suede if you're looking for maximum versatility.
If M.Gemi is known for one thing, it's craftsmanship — and these booties are no exception. Not only is The Christina crafted with luxe materials like Italian calf hair and Nappa leather, but they're also handmade at artisan workshops in Tuscany. And the quality of materials and construction shows: these booties fit like a glove right out of the box, with no need to break them in.
With nine striking shades to choose from, you're bound to find a pair you love — whether you prefer basics like black suede, eye-catching burgundy patent, or fun prints like python and leopard. I have the metallic gunmetal pair and they're surprisingly versatile: they instantly add some interest to a little black dress or a simple outfit of jeans and a bodysuit.
Read our full M.Gemi review.
Everlane remains our favorite place to buy the best women's workwear. The brand's clothing is a go-to for professional basics, but the shoe section can be something of a hidden gem.
We reviewed the Everlane Glove Boot right when it came out and have loved the style ever since.
"As the name of these ankle boots suggests, they fit like a glove because the upper is made with a stretchy ribbed knit fabric. Even when a pair of boots that fit my feet, I often find that the shaft is either too big or too tight — but that's not an issue here since they stretch and mold to my ankles and calves," I wrote in my most comfortable boots guide.
You can purchase logo and accolade licensing to this story here.
Disclosure: Written and researched by the Insider Reviews team. We highlight products and services you might find interesting. If you buy them, we may get a small share of the revenue from the sale from our partners. We may receive products free of charge from manufacturers to test. This does not drive our decision as to whether or not a product is featured or recommended. We operate independently from our advertising team. We welcome your feedback. Email us at reviews@businessinsider.com.
Advertisement