20 Best Ankle Boots That Are Both Functional and Fashionable

Best Overall

Blundstone Original 500 Chelsea Boot

View On Amazon $131 View On Nordstrom $210 View On Zappos $210

“I think everyone should own a pair of Blundstones,” fashion stylist Mecca Cox tells InStyle. “They look better the more you wear them and once you own them you’ll be shocked how much use you get out of them. They’re also snug on the ankle so it's a flattering shape without trying too hard.” Another one of our experts, Dr. Marien Zanyk and creator of Anklestone, recommends them as well. 

Blundstone’s Original Chelsea Boots are a sturdy option, made from water-resistant leather. The leather is breathable and molds to your foot shape while being extremely comfortable. The other secret to this classic design is the shock-absorbing power that this flat style offers, thanks to its shock protection technology — which helps reduce fatigue and orthopedic problems in the lower back, feet, and legs. A cushioned midsole adds even more support. “The thoughtful details, such as the double pull tabs and elastic contour, demonstrate a well-considered approach to ease of use and immediate comfort,” Dr. Zanyk adds.

Material: Leather; TPU outsole | Size: 5–11 | Colors: 7

Best Budget

STQ Combat Lace-Up Boots

View On Amazon $58

“Less expensive, these boots offer many features — custom fit laces, a convenient side zipper, reasonably strong, padded, upper ankle support, and a woolen, comfort topper,” Dr. Zanyk explains. “A good deal for the money.” STQ’s combat boot shape is made from vegan leather and has a lace-up front that is typical of the military-inspired style. “Crafted with style and color choice in mind, this boot combines trendiness with comfort, ensuring a cozy fit,” she adds. Details such as the quilted side panels, knitted ankle cuffs, and slip-resistant soles set this one apart from competitors. 

Classic colorways ensure this boot can be paired with everything in your fall and winter wardrobes. We recommend pairing it with a tailored, wool coat, chunky, cashmere turtleneck, floaty maxi skirt, and hosiery for a slightly bohemian look, or with a fair-isle knit, puffer jacket, and jeans for a mountain aprés-ski vibe. 

Material: Faux leather; rubber outsole | Size: 5–11 | Colors: 5

Best Heeled

Staud Ankle Boot

View On Staud.clothing View On Saks Fifth Avenue $395 View On Bloomingdales $395

“There is a reason these boots have been consistently selling out everywhere and now come in a plethora of colors,” fashion stylist Anna Jarema says. Staud’s Wally Ankle Boot is an editor favorite, but fashionistas aren’t the only ones who love this simple, short-heeled boot (with just 2.1-inch heel height). This pointed, rectangular-toed shape is a customer favorite as well with good reason. “Streamlined silhouette to elongate your legs? Check. Added height yet with a realistic walkable heel? Check. Polished, minimal, and versatile, these will earn their cost per wear in any wardrobe,” Jarema calls out. It’s the boot that does it all.  

And since the Wally has garnered such a cult following, it now is available in seven colors, styles, and materials (including suede and matte leather), allowing you to find the ideal boot for your style preference or lifestyle. When it comes to styling, these can be dressed up or down. “They easily work with just about anything from denim and trousers to dresses and skirts,” Jarema notes.  

Material: Goat leather, leather, abs | Size: EU35–EU42 | Colors: 7

Best Everyday

Re/Done Cavalry Boot

View On Shopredone.com

You might know Re/Done for its vintage-inspired denim, but did you know the brand makes shoes? The Calvary boot is a square-toed, ankle boot that is made in Italy in artisanal factories. The elasticated side panel makes pulling these slip-ons all the easier. Cox especially loves the metal, biker detail that is seen through the silver harness that wraps around this style. The low heel offers a little bit of lift but is short enough to still be walkable, making it an everyday essential.   

“I love this Re/Done one because it’s a little chunky and really helps bring a dress down to earth,” Cox says. “It lends effortlessness and ease to any outfit you pair it with — skirts, dresses, or jeans.” Choose from either black leather or caramel suede and see for yourself how easy it is to style them with everything. 

Material: Leather or suede | Size: EU35–EU41 | Colors: 2

Best Lace-Up

Jack Rogers Peyton Bootie

View On Amazon $168

“Known for its comfort and versatility, this boot combines style with functionality,” says Dr. Zanyk. Jack Rogers’ Peyton Bootie is a simple, lace-up style that comes in both suede and a matte, glossed leather option. A zippered side allows for easy on and off, without untying the laces every time you pull these on or off. “It is available in a beautiful oak color, as well as black, while offering the moderate heel height to provide a fashionable lift without compromising stability,” she notes. At just 1.2 inches, this heel height is extremely manageable. The lug sole offers grip and traction on everything from slick sidewalks to snowy terrain, so you are sure to have that extra touch of safety.

Since the style is a basic silhouette, it can be paired with everything from knit midi dresses to floaty maxi dresses and cropped denim. We're sure it will be a versatile player in your lineup.

Material: Leather; rubber outsole | Size: 6–11 | Colors: 2 

Best Knitted

Vivaia Regina Booties

View On Amazon $149

Looking for a leather alternative? Vivaia’s Regina Booties are made from a wool upper, which is both water-repellent and warm. The pull-on style is supremely comfortable, featuring a stable, 2.1-inch heel, spacious square toe, and an anti-slip rubber outsole. The best part is the natural Artemisia Argyi herbal insole, which is plant-based and provides pressure relief. The stretchy, wool upper also forms to the foot, so a perfect fit is always found. Cleaning is also quite easy since the uppers and soles can be scrubbed with a cloth both inside and outside.

When it comes to styling, we love that these boots can go from day to night with ease. Whether a cropped jean, a wide-leg trouser, or a midi skirt is your bottom of choice, this boot pairs perfectly with any of the above. The harder question really is which color to choose from the extensive line’s range. 

Material: Wool; rubber outsole | Size: 5–11 | Colors: 8  

Best Western

Reformation Otto Mini Western Boot

View On Reformation $398 View On Anthropologie $398

“For that Western spirit in all of us — from city streets to suburban towns — these boots feel timeless and fresh all at once,” Jarema says. Reformation’s Otto Mini Western Boot gives a modern twist to the cowboy boot. The ankle height keeps them from feeling too costumey (compared to, say, a knee-high), while classic colors and leathers without too many extra frills give them a wearable edge. The 2-inch block heel won’t strain or twist ankles and the snip, pointed toe is true to the cowboy design. 

To keep them in the now, be sure to pair these with closet classics that aren’t out of the normal for your style. “Keep it classic and pair them with straight-leg jeans and a tee for the weekend,” Jarema suggests. “Then take them through the seasons with denim shorts and oversized blazers in warmer months.” A look that is very much inspired by Princess Diana is a look we can get behind with fervor. 

Material: Leather | Size: 5–11 | Colors: 4  

Best Black

Red Wing Heritage 6" Classic Moc

View On Zappos $310 View On Redwingshoes.com

“The Red Wing Moc is just so classic and timeless,” Cox explains. “You can really wear it out and never worry about how to take care of it. The more worn it is, the better.” This boot was made for the rugged outdoors, with full-grain leather that is also water-repellent. This women’s version was constructed with softer leather than the original that dates back to 1952, making for an easier break-in period. However, it is also extremely lightweight, thanks to the signature hydrolysis-resistant polyurethane Traction Tred outsole, making it all the more wearable. 

Cos appreciates the versatility of this heritage boot. “A jean and a sweater, a jacket, and layers work really well with this style or even just a T-shirt,” she says. “It’s truly timeless and you can work outside around the house, go for a hike, or just wear them to a cute casual lunch. Sky’s the limit!”. 

Material: Leather; polyurethane outsole | Size: 5–12 | Colors: 11

Best Hikers

Orthofeet Dakota Hiking Boots

View On Amazon $130

If you are looking for some serious orthopedic function, Orthofeet’s Dakota Hiking boots are recommended by Dr. Zanyk. “This boot was made for support,” she says. “It has ‘the works’ for anatomical support, heel cushion, and an upper boot that is engineered with external reinforcement and performance toggle pulls to customize the closure your foot needs in a snug, yet anatomically contoured fit.” She also calls out the excellent arch support and padding the shape offers — making it an ideal, everyday choice to combat foot and heel pain, hammer toes, and other ailments.  

Not only is this boot anatomically sound, but it also has a clean and sporty design, with a lace-up closure and rubber sole. Whether a hike means a day-long excursion into the mountains, or simply a walk around your neighborhood park, these boots were definitely made for walking. 

Material: Leather; rubber outsole | Size: 5–12 | Colors: 2 

Best Warm

Dr. Martens Leonore Chelsea Boot

View On Amazon $180 View On Nordstrom $135 View On Publiclands.com

Cold feet can make or break a day. Sometimes the temperatures can dip so low that not even a double layer of socks with your everyday boots will retain heat like you need them to. That is where the Leonore Chelsea Boot from Dr. Martens comes in. The boot’s interior is lined with soft, faux fur, to keep you cozy and warm. Outside, the boot keeps true to the brand’s classic DNA with contrast topstitching and sturdy leather that withstands the elements — thanks to the oil and fat-resistant sole the brand is known for that is slip-resistant. No review is complete without mention of the air-cushioned soles, which are extremely comfortable and reactive, withstanding hours of wear.   

We will be wearing these boots with baggy jeans, oversized knits, leather gloves, and a puffer jacket on the weekend and pairing with a pleated skirt, blazer, and button-down for a daytime-appropriate look.   

Material: Leather | Size: 5–11 | Colors: 5  

Best Sustainable

Camper Pix Boot

View On Camper.com

If versatility, comfort, and ease are what you need, check out Camper’s Pix Boot — a style that offers it all. “That pair you keep by the door to easily slip into for quick runs to the market or walks with the dog,” Jarema says. “The flexibility to easily pull them on and off with added traction on the soles makes them a go-to for quick dashes out in any weather.” An Ortholite insole provides cushioning, making them extremely comfortable, but what we love most are the eco-friendly design elements of this shoe, such as recycled materials and Leather Working Group (LWG) certification, ensuring responsibly sourced and manufactured leather is used.

They are downright fashionable, too. The leather-blend upper is sleek and smooth, while the chunky, ridged EVA sole adds modern flair. Jarema suggests the blue sole variation for a pop of color, but they have more neutral tones as well, should that be your preference. “Pair them with sweatpants and an oversized bomber jacket to run your errands in style,” she recommends. 

Material: Leather, recycled polyester, latex; EVA outsole | Size: 5–11 | Colors: 6 

Best Leather

Labucq Joan Boot

View On Labucq.com

Labucq is a shoe brand that fashion insiders swear by. Founded and designed by Lauren Bucquet, an ex-Rag & Bone designer alum, Bucquet launched her own brand with the intention of fulfilling a niche in the direct-to-consumer marketplace. She crafts beautiful, designer-quality shoes in a small factory in Italy, never sacrificing high-quality production or special design details.      

“I like this one from Labucq because it’s chunky yet refined,” Cox says of the brand’s Joan Boot. Featuring a thicker, 2-inch block heel, the boot has a clean design, with a rounded, pointed-toe and an inside zipper closure for easy wear. Handmade in Tuscany, the high-quality leather will just wear well with time and the styling options are endless. Cox appreciates that they’re great for short or long dresses but can also be dressed up or down with jeans or trousers. It’s a boot that will take you to many places.  

Material: Leather, rubber inset | Size: EU35–EU43 | Colors: 5 

Best Buckled

Ganni Double Buckle Cut-Out Ankle Boots

View On Nordstrom $495 View On Farfetch.com $382 View On Ganni.com

Ganni’s signature, Danish design sensibilities are always on point when it comes to its ready-to-wear, accessories, and shoes. “Designed in the brand’s quintessential style, these buckled boots are spot on to fill that trend craving you’ve had all season,” Jarema says. This double-buckle, cut-out boot perfectly demonstrates the brand’s unique aesthetic and attention to detail. If you were a fan of its cowboy boot, then this might be your new favorite. A pointed toe, metal buckle details aplenty, and a low, block heel round out the smart design elements.

“Edgy yet polished, they look great with floral dresses and denim alike,” Jarema says. “Try wearing them with thin socks and a miniskirt to really lean into the trend this season, then into spring.” We also recommend wearing these with ribbed tights in chillier climates, when a little extra warmth is needed for the winter months ahead. 

Material: Recycled polyester | Size: 5–12 | Colors: 1  

Best for Date Night

Loeffler Randall Thandy Curved Heel Boot

View On Saks Fifth Avenue $395 View On Loefflerrandall.com

You can’t go wrong with a sleek, heeled boot that can dress up any look in an instant. Loeffler Randall’s Thandy boot was designed with a chic, curved heel that feels very relevant at the moment. The pointed toe and tug, sock-like upper creates a smooth line that is very stylish. A padded footbed ensures that comfort is top of mind, for long hours of wear, and the 2.75-inch heel height is tall enough to give lift but won’t have you in pain all day either. 

“I think this Loeffler Randall is a great price point for a really chic boot you can get a lot of wear out of,” Cox explains. “This one would look great with a dress and tights or a blazer or all of the above and the little heel shape detail makes it special.” Snag yours before these boots go very quickly. 

Material: Leather | Size: 5–12 | Colors: 2 

Best for Narrow Feet

Thursday Boot Co. Captain Lace-Up Boot

View On Thursdayboots.com

If you have narrow feet, Dr. Zanyk recommends checking out Thursday Boot Co.’s Captain Lace-Up Boot. “For narrow feet, this boot offers a secure fit without sacrificing style,” Dr. Zanyk says. “The snug design around the heel and instep prevents unwanted movement.” These are not the only functional design details, either. Handcrafted with Goodyear welt construction (making them water-resistant and resoleable), Poron antimicrobial, shock-absorbing insoles, and cork-bed midsoles that form to your feet, they are built with longevity and comfort in mind. 

“Stylish for women and men [they carry the same design in both size ranges], this ankle boot is a quality choice in rugged, yet flexible leather,” Dr. Zanyk adds. Choose from 10 different colorways and fabrications — from the rugged and resilient to classic and a lug sole version. This is one boot that is certainly worth investing in. 

Material: Leather; rubber outsole | Size: 5–12 | Colors: 10

Best Brown

Frye Harness 8R Booties

View On Saks Fifth Avenue $458 View On Thefryecompany.com

An American-based brand that is known for its heritage craftsmanship, Frye’s signature Harness 8R Booties have an oiled leather exterior that is timeless and a harness design that is synonymous with the brand. “A forever classic, these harness boots add an instant cool girl edge to any look,” Jarema says. “As they look better and better with time, are built to last, and definitely worth the investment, you’ll easily wear them through the seasons.” 

A square toe, a stacked heel (measuring just 1.75 inches), and a Goodyear welt construction are just a few of the extra standout design details. The pull-on style also has a wider calf area, for those who are worried about the cut. The rubber sole also will help resist water and the other elements should you encounter. Jarema suggests pairing these boots with jeans and sweaters in fall and winter and flowy dresses and skirts in warmer months, truly making it a style that can be worn year-round. 

Material: Leather; rubber outsole | Size: 5–12 | Colors: 3

Best Waterproof

Sam Edelman Laguna Waterproof Chelsea Boot

View On Amazon $170 View On Nordstrom $111 View On Bloomingdales $119

For many of us, boots are worn primarily in the cooler months, when extra precipitation and colder temperatures require additional protection. Sam Edelman’s lug-sole boot is waterproof, offering a little respite from the elements. “With iconic pull tabs, conforming elastic, and also, with a sturdy sole designed for grip in foul weather, the Laguna Chelsea Boot offers both style and practicality,” Dr. Zanyk says. “With a design that excels in both aesthetics and functionality, this boot provides a well-made solution for inclement weather, even for wide widths.” 

The traditional, utilitarian shape gives the wearer a little lift thanks to a stacked heel and sole. And, with endless leather and color options, you can go with the tried-and-true, classic blacks and browns or try funkier versions like buttery Sesame or embossed snakeskin. We will be wearing these with everything from blazers, tee, and jeans, to trouser pants and leather jackets, for something different. 

Material: Leather; polyurethane midsole; and rubber outsole | Size: 5–14 | Colors: 15  

Best Suede

Aeyde Zoe Suede Ankle Boots

View On Shopbop.com $495 View On Aeyde.com View On Net-a-Porter $495

It was love at first sight when we saw these Aeyde suede ankle boots. The Zoe style is a pointy, kitten heel boot that is an editor favorite (and also available in black matte leather, should you prefer!). The brand was founded in Berlin in 2015 by Luisa Dames and has quickly become a fashion favorite thanks to its clean aesthetic and affordable price points. The Zoe Ankle Boot represents this design philosophy quite well. Quality for the brand is also of utmost importance, as each pair is made in a family-run factory in Italy. 

We envision wearing these with skinny trousers or pants or a cropped silhouette to really show off the luscious design of the zip-back boot. For work, we would pair a full suit look with these pointy boots and for an easy date night outfit, toss on with a cropped flare jean, turtleneck sweater, and hoop earrings. 

Material: Cowhide suede | Size: EU35–EU42 | Colors: 1 

Best Rain

Sorel Duck Boot

View On Amazon $91 View On Nordstrom $100 View On Sorel.com

Sorel’s Out ‘N About III boot was made for just that. If you're looking for a fashionable rain boot, its waterproof style will allow you to face the elements, with all-day comfort. Whether you’re facing wind, rain, or even light snow showers, the weatherproof exterior and thick, grippy rubber sole make it a great option to keep you stable and sturdy with plenty of traction. This is especially helpful for those city dwellers whose commute often includes a lot of walking. A removable, molded EVA footbed means that comfort won’t be sacrificed when you’re moving in these for hours on end — whether running errands or touring a new city. 

Style is not compromised either, for this functional shoe. The lace-up design and thick sole give off a sporty, cool look and there are so many color choices to pick — from plain black to a punchy orange — finding something that fits your personal style aesthetic is easy. We will be pairing these with everything from jeans to cropped trousers, leggings, sweatpants, and more. 

Material: Leather, suede; ethylene vinyl acetate outsole | Size: 5–12 | Colors: 25