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The most comfortable ankle boots we own include styles you can wear while walking all day to dressy heeled pairs.
Samantha Crozier, Gabrielle Chase/Business Insider
I’m not thrilled by pumpkin spice lattes (don’t come for me), but as autumn approaches and the temperatures start dipping, I do get a little overeager to pull my ankle boots from storage. They have a unique way of anchoring a whole look, either by balancing out chunky sweaters, elevating a simple jeans-and-tee combo, and offering just the right amount of protection during hard-to-predict forecasts.
A quick look at some of our favorite ankle boots:
Best overall: Naturalizer Delaney Ankle Bootie is our favorite wear-with-anything boot, with a walkable 2.38-inch block heel, cushioned arch support, and wide-width options.
Best for wide feet: The stretchy, water-repellent Vivaia Regina Pro has a roomy fit, a comfortable pressure-relief insole, and a fun sock-boot silhouette.
Best for winter: The Blundstone Thermal Chelsea Boot keeps feet warm and dry with a shearling insole, waterproof construction, and a grippy sole for slush and slick sidewalks.
Best budget pick: Dream Pairs Classic Chelsea Ankle Boots are an easy, under-$50 everyday option with pull tabs and stretchy side panels.
As a style writer, I’ve tested too many ankle boots to count. Some I tore off before I even left the house. Others I excitedly bust out year after year.
The pairs I keep coming back to tend to have a few things in common: They’re comfortable enough to keep my feet happy for long hours, durable enough to withstand more than one season of wear, and are versatile enough to dress up or down.
Here are the booties that check all those boxes. And if you’re in the market for boots with a taller shaft, see our guide to the best knee-high boots .
Editor’s note: Every ankle boot in this guide has been tested by a member of our team in real-world settings, from commutes and errands to dinners and long city walks. We assess comfort, fit, support, traction, materials, durability, and value, updating our recommendations as we test new styles. Read more about how we test clothing, shoes, and accessories .
Best overall: Naturalizer Delaney Ankle Bootie
Rebecca Strong/Business Insider
What we love:
Reasonable heel height (2.38 inches)
Hidden stretch to accommodate wider calves
Super comfy, thanks to cushioning and arch/heel support
Breathable lining
Versatile enough to pair with workwear, jeans, or dresses, or workwear
Available in wide width
Skip these if:
You prefer a more rugged/casual look
You’re looking for a truly all-day walking boot
I’m a very specific shopper—I know exactly what I want, and I won’t settle until I find it. (It’s why, much to my husband’s amusement, I’ll often take one look around a store with endless options and leave empty-handed.) For years, I’ve been on the hunt for a wear-with-anything bootie that didn’t make my arches ache after a couple of hours. The Naturalizer Delaney is it.
It has a just-right block heel height—between 2 and 3 inches—and a sleek, sculpted aesthetic. These booties go with everything , too: I’ve been wearing them with straight-leg jeans, sweater dresses, and ponte leggings alike.
It’s the thoughtful, comfort-forward features that make these ankle boots really stand out, though. Between the ultra-plush foam cushioning, the pressure-relieving heel and arch support, the sculpted insole, and the breathable lining, these are genuinely realistic to wear for extended periods of time. I also appreciate the hidden gore at the side seam, which allows these booties to stretch and
Best Budget: Dream Pairs Classic Chelsea Ankle Boots
Rebecca Strong/Business Insider
What we love:
Surprisingly high quality for the price
Classic Chelsea silhouette works with a wide range of casual/everyday outfits
Super easy pull-on design
Skip these if:
Genuine leather construction or premium finishing is a priority
You want a polished boot for dressier occasions
I’ve owned and loved several pairs of shoes from Dream Pairs. Despite the budget-friendly price points, the products have consistently held up pretty well—and these Chelsea Ankle Boots are no exception. Synthetic leather can be dicey from an aesthetic standpoint, but I suspect these boots could fool most. By far my favorite features are the elastic goring and pull tabs, which allow me to slip these on and off in a matter of two seconds flat.
I might be more likely to splurge on heavy-duty snow boots or dress boots I’m pairing with more formal pieces—but when it comes to a casual, everyday boot, I love a budget-friendly workhorse. The Dream Pairs Chelsea ankle boots definitely have a laidback look, but I was pleasantly surprised to find that they work just as well with midi skirts and slip dresses as they do with cuffed jeans.
Best for wide feet: Vivaia Regina Pro
Samantha Crozier
What we love:
The stretchy fabric makes them easy to pull on and roomy enough for wider feet
They held up well in a light drizzle
They give you the sock-boot look without the designer price tag
Skip these if:
You need a boot for heavy rain
You prefer a structured leather boot over a close-fitting sock style
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 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
For more of our thoughts on the brand, see our full Vivaia review.
Most packable: M.Gemi The Una Bootie
Gabrielle Chase/Business Insider
What we love:
Square-toe with stitched center seam
Lightweight and sleek
Can squeeze into tight luggage space
Skip these if:
You need heel cushioning or arch support
You have extra wide feet or ankles
M.Gemi has taken everything I love about its Una ballet flats and translated it into a walkable ankle boot. While practically flat, this style is more suitable for long distances because of the tiny heel and rubber sole inserts.
For most of my time as a city-dweller, I’ve stayed away from statement boots because their weight make my legs tired. These are instead a sock-like bootie that feels like wearing next to nothing. One Saturday I wore them straight out of the box to walk 12,000 steps across Brooklyn, and the soft, unstructured suede left me with zero blisters.
I wear a size US 8 and ordered the EU 38.5. I usually go up to a 39 in European sizing, but these fit perfectly true to size. My feet are a regular width and the slightly tapered square-toe feels comfortable, but people with wide feet may find them too slim (same goes if you have wide ankles — the boot shafts are on the narrow side, too).
These are a highly packable ankle boot because the foldable leather takes up little space and the minimal silhouette is easy to style. However, they won’t offer much warmth in winter and the insoles lack arch support (or any cushioning for that matter). Nevertheless, I wear the Una Booties constantly because they slip on effortlessly. Plus, the taupe colorway is a dove gray that’s perfect for low-contrast fall outfits. — Gabrielle Chase, style editor, Insider Reviews
Read more in our M.Gemi review .
Best Chelsea boot: Thursday Boot Company Legend Platform
Rebecca Strong/Business Insider
What we love:
Substantial leather construction
Lugged platform offers a cooler, more modern look
Supportive, cushioned underfoot
Available in wide width
Skip these if:
You dislike chunky soles
You’re looking for a sleek, lightweight Chelsea
You need something dressy enough for the office
I recently went down quite a Google rabbit hole about the history of Chelsea boots and learned that the style dates back to the 1830s, when Queen Victoria requested that her personal bootmaker (can I have one of those?) craft a comfortable walking and riding boot without laces that could get caught in her stirrups. By the mod scene of the ’50s and ’60s, the style had entered the fashion mainstream in London’s trendy Chelsea neighborhood—hence the name. Chelsea boots have remained popular ever since, and I don’t expect they’ll ever go out of style. That’s why I’m a proponent of investing in a durable pair that ages like a fine wine.
Thursday Boot Company’s Legend fits the bill. The high-quality leather upper looks better with time, the lug rubber platform outsole gives me a nice leg-lengthening lift yet feels ultra-sturdy on any surface, and the shock-absorbing memory foam insoles kept my feet from feeling fatigued during step-intensive days.
I own these in Black Matte, which has a uniquely soft almost nubuck-like finish—it makes them feel a little edgier and more sophisticated. I’m a huge proponent of “wrong shoe theory,” so I defiantly wear these with flowier, ultra-feminine clothing for some unexpected contrast. That said, they work especially well with leggings and straight-leg denim.
Best water-resistant: Vionic Aria 2.0 Wedge Ankle Bootie
Rebecca Strong/Business Insider
What we love:
Water-resistant upper
Wedge offers a compromise between height and stability
Lugged outsole provides solid traction
Supportive footbed
Skip these if:
You need a waterproof boot for heavy rain or snow
You prefer a more delicate silhouette
Shopping for boots in my 30s has been a distinctly different experience than it was in my previous decade of life. I suddenly find myself seeking out marketing terminology I never paid attention to before (orthotic technology! Arch support!). That’s precisely why Vionic caught my eye: The brand was founded by a podiatrist, its shoes incorporate proprietary technology developed with input from medical professionals, and many styles have earned a seal of acceptance from the American Podiatric Medical Association. In other words, these are shoes designed to feel really good, not just look really good.
The first time I slipped on the Aria 2.0 , I almost audibly gasped at how comfortable they were. Even on my absurdly wide feet, they felt practically custom-made. The 2.25-inch wedge gives my 5-foot-4 frame a little boost without making me feel unstable, and the Mulled Wine suede is such a refreshingly bold change from my usual black and brown boots, yet surprisingly versatile for such a rich shade.
Like many of Vionic’s other booties, these feature contoured arch support, shock-absorbing cushioning, and a deep heel cup. I’ll be wearing mine with everything from leather leggings to midi dresses and denim skirts.
Best for cold weather: Blundstone Thermal Chelsea Boot
Amir Ismael/Business Insider
What we love:
Warm shearling insoles make cold, slushy days much more tolerable
Waterproof construction means you don’t have to dodge puddles or snowbanks
The rugged sole has great traction, even on rocky trails
Pull tabs and stretchy ankle panels make them easy to get on and comfortable to wear
Tough enough for winter errands, dog walks, and light hikes
Skip these if:
You want a more streamlined, dressy-looking ankle boot
You plan to wear thick socks, but don’t want to size up a half size
Insider Reviews’ executive editor Sally Kaplan deems these Blundstones the ultimate ankle boots for winter weather. “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.
Best kitten heel: Marc Fisher Danai Kitten Heel Leather Ankle Bootie
Rebecca Strong/Business Insider
What we love:
Sleek, polished silhouette
Modest 1.73-inch heel
Works equally well with trousers, skirts, and dresses
Available in a wide variety of colors and finishes (patent leather, suede, snake printed leather, etc.)
Skip these if:
You want substantial support and cushioning
Traction is important to you
You prefer chunkier styles
It’s hard to find a boot that feels classic yet current, and comfortable yet chic—but that’s exactly what the Marc Fisher Danai accomplishes. So, it should come as no surprise that this shoe has repeatedly sold out, and the brand keeps bringing it back.
I love that the dainty kitten heel on these booties still elongates my legs slightly without putting too much pressure on the balls of my feet. Plus, the modest heel height makes them feel office-friendly, although they transition seamlessly to after-work drinks. The square toe is surprisingly roomy, and the shiny side zipper doesn’t just make them effortless to pull on and off—it also adds a little visual interest.
Whether I’m wearing the Danai with a mini dress, wide-leg trousers, or split-hem jeans, I always feel put-together with these on.
Best snip toe: Cole Haan Blanche Snip Toe Booties
Cole Haan
What we love:
Flattering, elongated snip toe
Block heel feels sturdy to walk in
Polished enough for work or going out
Responsive cushioning and forefoot padding
Skip these if:
You need a ton of room in the toe box
You’re looking for a strictly casual, everyday boot
I could easily write a love letter to a snip toe—the narrower, elongated shape flatters my foot without crushing my toes the way a fully pointed toe would. A snip toe feels sharper and dressier than a round toe, but still retains an easygoing, Western-inspired vibe that can be dressed down.
Wearable but still fashion-forward, the Cole Haan Blanche is the kind of boot I know I’ll be reaching for over and over again, and for many seasons to come. The block heel feels stable but not chunky, and the toplift provides a surprising level of traction while protecting the main block from wearing down. Cole Haan says these were designed with “responsive cushioning” to absorb shock on impact, and I do notice a difference when my feet hit harder surfaces like pavement. There’s also a decent amount of forefoot padding, which helps minimize pressure on the balls of my feet.
All the practical features aside, these just look luxurious. And they’re versatile, too: They don’t look out of place with relaxed-fit jeans and a slouchy sweater or with a blazer dress and tights.
Best splurge: Scarlett Chase Portia 75 Stretch Bootie
Samantha Crozier/Insider
What we love:
Three-inch stiletto booties that somehow feel more like sneakers
Built-in arch support and plenty of padding keep your feet from aching after a few hours
The suede upper and pointed toe make them feel special enough for dinner, weddings, and nights out
Made in the same factory as Jimmy Choo, with the construction to justify the splurge
A rare high heel you can actually stay in all night
Skip these if:
You want a budget-friendly bootie
You need the extra stability of a block heel or platform
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
Best dressy: M. Gemi The Christina
Samantha Crozier/Business Insider
What we love:
Handmade in Tuscany from beautiful materials, including Nappa leather and Italian calf hair
They fit comfortably right out of the box, with no break-in period
Nine color and finish options, from black suede to burgundy patent and leopard print
Skip these if:
You’re looking for a simple, low-key everyday boot
You prefer to keep your shoe budget under $400
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 .
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