The Best Ankle Boots for Women, Rated for Comfort and Style

The best ankle boots for women feel good at hour eight, survive a wet sidewalk, and still look right with the jeans and dresses you already own. We pulled twenty pairs from brands you know, from Blundstone and Sam Edelman to Tory Burch and UGG, and sorted them by what each one does best. You will find Chelsea boots, lug soles, western booties, kitten heels, sock boots, and a few pairs built for real rain.

Every pick gets four scores out of five, for comfort, walkability, dress up range, and weather. Each boot also comes with a short note on who should skip it, because a gorgeous heel is no help if your day involves a mile of pavement. Start with the Blundstone at the top if you only want one pair, then work down the list for heels, rain boots, and the fun ones.

Best overall ankle boot

1. Blundstone Classic 585 Chelsea Boot in Rustic Brown

Comfort

5/5

Walkability

5/5

Dresses up

2/5

Weather ready

4/5

Blundstone built the Classic 585 from rustic brown premium leather that is water resistant, then lined it in leather for a relaxed fit from the first wear. A removable footbed with XRD Technology in the heel absorbs up to 90 percent of walking impact, and an extra set of Cambrelle footbeds lets you fine tune the fit. That shock absorption, the easy pull-on Chelsea shape, and reinforced stitching at the heel and gusset are why it takes the top spot.

Wear these with straight jeans, a chunky sweater, and a barn jacket for the most classic fall uniform there is. They also look great under a midi skirt with thick tights, which softens the rugged sole. On days that call for more polish, swap to the dark chocolate Cole Haan Chelsea boots for the same easy shape with a sleeker profile.

Skip it if: Skip it if you want a boot that reads dressy, since this one is happiest with denim.

Shop it at Blundstone

Best everyday suede bootie

2. Sam Edelman Petty Ankle Boot in Black Suede

Comfort

4/5

Walkability

4/5

Dresses up

3/5

Weather ready

2/5

Sam Edelman's Petty is a low suede bootie with a stacked 1.5 inch heel and a side zip that makes it simple to get on and off. The footbed is lightly cushioned, and the 4.5 inch shaft sits just above the ankle, so it works with cropped and full length pants alike. It gives you a small lift you can wear all day, which makes it our pick for the most wearable suede pair.

Pair the Petty with black skinny jeans, a long cardigan, and a crossbody for errands that turn into lunch. It also looks sweet with a floral midi dress and bare legs on a mild fall afternoon. If you like the shape but want more heel, the black suede Loeffler Randall Isla is its dressier older sister.

Skip it if: Skip it if you live somewhere wet, since suede and puddles do not mix.

Shop it at Zappos

Best waterproof Chelsea boot

3. Cole Haan Grand Flex Fenella Chelsea Waterproof Bootie in Dark Chocolate

Comfort

4/5

Walkability

5/5

Dresses up

3/5

Weather ready

5/5

Cole Haan made the Fenella with waterproof leather and sealed seams, so a rainy commute is no longer a reason to wear sneakers. A foam footbed with a leather lining sits over a rubber outsole, and the 45 mm heel gives a little lift without any wobble. Add Grand Flex Technology and you get a Chelsea boot that handles weather far better than most fashion pairs.

Dark chocolate leather goes with nearly everything, from black trousers to blue jeans to a camel coat. Try it with wide leg jeans that skim the top of the boot and a cream fisherman sweater. For a tougher look with the same waterproof build, the black Cole Haan lace-up version adds a buckle at the ankle.

Skip it if: Skip it if you only want a slim, dressy heeled bootie.

Shop it at Cole Haan

Best low block heel

4. Loeffler Randall Roxy Ankle Bootie in Espresso

Comfort

4/5

Walkability

4/5

Dresses up

4/5

Weather ready

2/5

Loeffler Randall cut the Roxy from espresso brown stretch nappa leather, so it follows the line of your ankle instead of gaping. Its 2 inch stacked block heel is low enough for a full day, and a padded leather footbed adds comfort underfoot. A concealed side zipper keeps the outside clean, which is exactly what you want from a heeled boot you reach for constantly.

Wear the Roxy with slim cropped trousers and a fitted turtleneck for the office. On weekends it looks just as good with straight jeans and a suede jacket. Espresso reads softer than black, and it sits nicely next to the light brown Tory Burch cap toe boots if you are building a brown boot wardrobe.

Skip it if: Skip it if you need a boot for slush or heavy rain.

Shop it at Loeffler Randall

Best lug sole Chelsea

5. Steve Madden Hutchh20 Chelsea Lug Bootie in Black

Comfort

4/5

Walkability

4/5

Dresses up

2/5

Weather ready

4/5

Steve Madden's Hutchh20 pairs a sturdy lug sole with a water resistant upper made of textile and vegan leather. The 2.5 inch heel is built into that chunky sole, so you get height without balancing on a skinny heel. A 5.5 inch shaft and a Chelsea shape make it a quick boot to pull on for gray, drizzly days.

Try it with black leggings, an oversized sweater, and a puffer vest for a sporty weekend look. The lug sole also gives a pleated midi skirt a cool, tough contrast. If you love the shape but want full waterproofing, the dark chocolate Cole Haan Chelsea is the upgrade.

Skip it if: Skip it if you want a boot made of real leather.

Shop it at Steve Madden

Best waterproof heeled bootie

6. Dolce Vita Soline H2O Bootie in Black Leather

Comfort

3/5

Walkability

4/5

Dresses up

4/5

Weather ready

5/5

Dolce Vita gave the Soline H2O a waterproof design, a genuine leather upper, and a durable rubber outsole, which is rare for a bootie this sharp. A pointed toe, a traditional stacked 2.3 inch block heel, and a side gore panel give it a subtle western feel. It is the boot to grab when the forecast says rain but the plan says dinner.

Wear it with dark flared jeans and a black blazer for a polished night out that can survive a storm. It also works with a knit midi dress and opaque tights. For a more openly western look, the brown Tecovas Daisy takes the cowboy details further.

Skip it if: Skip it if pointed toes pinch your feet.

Shop it at Dolce Vita

Best western bootie

7. Tecovas The Daisy Zip Bootie in Scotch Goat

Comfort

4/5

Walkability

3/5

Dresses up

4/5

Weather ready

2/5

Tecovas built the Daisy from goat leather that the brand says breaks in quickly and develops a patina fast. It has a snip toe, a 2.5 inch angled leather heel, a leather lined shaft, and an inside zipper, so you skip the tug of a classic cowboy boot. The signature toe bug stitching and leather outsole make it the most authentic western pair on this list.

Pair the Daisy with light wash straight jeans, a white tee, and a suede jacket for an easy fall weekend. It also looks great peeking out from under a flowy prairie midi dress. Keep the rest of the outfit simple and let the warm brown leather do the talking.

Skip it if: Skip it if you need grip on wet streets, since the sole is leather.

Shop it at Tecovas

Best flat lace-up boot

8. Clarks Desert Boot in Sand Suede

Comfort

4/5

Walkability

4/5

Dresses up

2/5

Weather ready

1/5

Clarks launched the original Desert Boot in 1950, and the design has barely changed since. Sand suede, a breathable leather lining, and an unfussy lace fastening sit on the brand's signature crepe sole. It is the flat, low lace-up for anyone who wants comfort and an easy, worn in look.

Wear it with cuffed straight jeans, a striped tee, and a navy chore coat. It also pairs well with wide leg trousers and a chunky cardigan for a relaxed weekend. For colder, wetter days, trade up to the black Cole Haan lace-up boots, which keep the laced look and add waterproofing.

Skip it if: Skip it on rainy days, since suede and crepe soles do not like water.

Shop it at Clarks

Best for the office

9. Everlane The City Boot in Black

Comfort

3/5

Walkability

4/5

Dresses up

4/5

Weather ready

2/5

Clean and simple, Everlane's City Boot is a black leather boot with a 1 7/8 inch heel, an interior nylon zipper, and a nappa pull tab. The leather comes from an LWG Gold certified tannery, and the outsole and welt are made of reconstituted leather. That plain shape and modest heel make it an easy pick for long days at a desk and short walks to meetings.

Wear it with black ankle trousers, a crisp white shirt, and a long camel coat. It also looks sharp with a knee length pencil skirt and sheer black tights. If your office leans casual, swap in the espresso Loeffler Randall Roxy for a softer brown take on the same idea.

Skip it if: Skip it if your commute involves rain, since the outsole is leather based.

Shop it at Everlane

Best combat boot

10. Dr. Martens 1460 Women's Smooth Leather Lace Up Boots in Black Smooth

Comfort

3/5

Walkability

4/5

Dresses up

2/5

Weather ready

3/5

Doc Martens fans know the 1460 by its yellow stitching, grooved sides, and scripted heel loop. It is Goodyear welted for durability, with a breathable textile lining, a lightly cushioned footbed, and an AirWair air cushioned outsole that resists oil and fat and has good slip resistance. The heel is a low 1.25 inches and the shaft is 6.5 inches, which makes it the toughest everyday lace-up here.

Pair the Docs with a slip dress and an oversized cardigan for the classic soft and tough contrast. They also work with black jeans, a plaid flannel, and a leather jacket. For a gentler laced look, the sand suede Clarks Desert Boot is the softer cousin.

Skip it if: Skip it if you want a boot that slips on, since this one laces all the way up.

Shop it at Zappos

Best splurge pair

11. Tory Burch Cap-Toe Low-Heel Ankle Boot in Light Brown

Comfort

4/5

Walkability

3/5

Dresses up

5/5

Weather ready

1/5

Tory Burch made this boot in supple light brown napa leather, lined it in napa too, and finished it with a contrast leather cap toe and a block heel of about 2 inches. A cushioned leather footbed and a napa pull on the zipper add to the polish. It is the most refined pair on this list, and the two tone toe makes even jeans look dressed up.

Wear it with cream wide leg trousers and a black turtleneck to echo the dark toe. It also pairs beautifully with a camel midi skirt and a fine knit sweater. Keep this pair for dry days and lean on the dark chocolate Cole Haan boots when the weather turns.

Skip it if: Skip it if you need grip, since the sole is buffed leather.

Shop it at Tory Burch

Best kitten heel

12. Dolce Vita Karlie Bootie in Espresso Suede

Comfort

3/5

Walkability

3/5

Dresses up

5/5

Weather ready

2/5

An ultra pointed toe and a 2 inch kitten heel define the Dolce Vita Karlie, cut from genuine suede in a deep espresso. The shaft is a fitted 5.9 inches, and a durable rubber outsole gives a bit more grip than a dress boot usually has. It is a small heel with a big dressy payoff, which is why it wins the kitten heel slot.

Wear the Karlie with straight leg jeans and a cropped sweater, or with a sleek maxi dress for evening. Espresso suede looks especially good against cream, camel, and burgundy. If you want a similar fitted shape in black, the Clarks Edina Stretch is a close match.

Skip it if: Skip it if you walk a lot on uneven streets.

Shop it at Dolce Vita

Best sock boot

13. Clarks Edina Stretch Ankle Boot in Black Suede

Comfort

4/5

Walkability

3/5

Dresses up

4/5

Weather ready

1/5

Clarks calls the Edina Stretch a heeled sock boot, and the premium black stretch suede upper hugs the ankle like one. A 2 inch heel, a chipped toe, and a 6.3 inch shaft keep it sleek, while a leather lined Contour Cushion footbed adds support. A subtle side zip means you never have to wrestle it on.

Tuck it under flared trousers so only the toe peeks out, or wear it with a short sweater dress and black tights. It is also a smart match for leather leggings and a long blazer. For a higher heel with the same stretch suede idea, look at the black Loeffler Randall Isla.

Skip it if: Skip it if you want a boot for rain or snow.

Shop it at Clarks

Best waterproof lace-up

14. Cole Haan Grand Flex Fenella Buckle Lace-Up Waterproof Bootie in Black

Comfort

4/5

Walkability

5/5

Dresses up

2/5

Weather ready

5/5

Waterproof leather and sealed seams make Cole Haan's lace-up Fenella a true foul weather boot, with a rubber outsole and a 45 mm heel. An ankle zipper means you can leave the laces tied and still get in quickly. A foam footbed, a leather footbed lining, and Grand Flex Technology make it a combat style boot you can wear all day.

Wear it with black jeans, a quilted jacket, and a beanie on cold, wet mornings. It also gives a plaid wool skirt and tights a tougher edge. On dry weekends, the sand suede Clarks Desert Boot is a lighter laced partner for it.

Skip it if: Skip it if you want something delicate, since this one reads utilitarian.

Shop it at Cole Haan

Best cushioned pull-on heel

15. Rothy's The Classic Boot in Black

Comfort

5/5

Walkability

4/5

Dresses up

3/5

Weather ready

3/5

With a structured, water resistant black upper that has a bit of stretch, the Rothy's Classic Boot moves with your foot instead of fighting it. The In Love Insole adds heel to toe cushioning, and a lightweight rubber outsole brings durable traction. A sleek 1.5 inch block heel, an inner pull tab, and stretch gore panels make it the easiest heeled boot to pull on here.

Wear it with black leggings and a long tunic sweater for travel days. It also looks neat with cropped kick flare jeans and a short trench. For a leather take on a sleek black boot, the Everlane City Boot is the natural next step.

Skip it if: Skip it if you want a boot with a sharply pointed toe.

Shop it at Rothy's

Best tall block heel

16. Steve Madden Harden Bootie in Black Leather

Comfort

2/5

Walkability

2/5

Dresses up

5/5

Weather ready

1/5

For real height, Steve Madden's Harden pairs a leather upper with a pointed toe and a 3.75 inch block heel. The wide heel offers more support than a stiletto, and an inside zipper makes it quick to put on. It is the tallest block heel on this list, so it is our pick when you want serious lift for a night out.

Wear the Harden with a black slip skirt and a cropped leather jacket for dinner and drinks. It also lengthens the leg under wide leg trousers that just graze the floor. Keep the black Steve Madden Hutchh20 for daytime and save this pair for after dark.

Skip it if: Skip it if you are on your feet all day.

Shop it at Steve Madden

Best stretch suede heel

17. Loeffler Randall Isla Ankle Bootie in Black Suede

Comfort

2/5

Walkability

2/5

Dresses up

5/5

Weather ready

1/5

Black stretch suede gives the Loeffler Randall Isla a close, sleek fit, set off by a pointed toe and a 3.5 inch heel. A padded footbed with a gold stamped logo softens the height, and a side zipper handles the rest. Of all the heels here, it is the one that feels most like an evening shoe.

Wear it with a black satin midi skirt and a soft cashmere sweater for holiday parties. It also turns basic black jeans and a silk cami into a date night outfit. For a lower heel in a similar fitted shape, the Clarks Edina Stretch is the daytime version.

Skip it if: Skip it if a 3.5 inch heel is more than you want to walk in.

Shop it at Loeffler Randall

Best square toe bootie

18. Vince Camuto Sybren Bootie in Rich Mahogany

Comfort

3/5

Walkability

3/5

Dresses up

4/5

Weather ready

2/5

A squared off toe sets the Vince Camuto Sybren apart, along with a subtle western inspired curved panel and an extra chunky block heel. Rich mahogany sits between brown and burgundy, so it adds color without feeling loud. That chunky heel is easier to balance on than a slim one, and the square toe looks current with wider pants.

Pair the Sybren with flared denim and a cream turtleneck for an easy weekend look. It also pulls together a flowy midi skirt and a cropped cardigan for brunch. Mahogany mixes well with the espresso Dolce Vita Karlie if you like layering brown tones across your boot collection.

Skip it if: Skip it if you prefer a classic almond or pointed toe.

Shop it at Vince Camuto

Best cozy flat boot

19. UGG Classic Mini II in Chestnut

Comfort

5/5

Walkability

4/5

Dresses up

1/5

Weather ready

3/5

UGG makes the Classic Mini II from twinface sheepskin suede with 17 mm of sheepskin lining and insole, so it is about as warm as an ankle boot gets. It is treated to be water resistant and stain resistant, and the Treadlite by UGG outsole adds traction, cushioning, and flexibility. With a 1 inch heel and a 5 inch shaft, it is the coziest pair on this list.

Wear it with leggings, a long fleece, and a knit beanie for chilly errands. It also looks fresh with straight jeans and a chunky cardigan. When you need more weather protection, switch to the black Sorel Chelsea rain boots.

Skip it if: Skip it if you want a boot you can dress up for work.

Shop it at Zappos

Best rain boot

20. Sorel Out N About IV Chelsea Rain Waterproof Boot in Black/Sea Salt

Comfort

3/5

Walkability

4/5

Dresses up

1/5

Weather ready

5/5

Puddles are no problem in Sorel's Out N About IV Chelsea Rain, which has a high gloss rubber upper and waterproof protection. A fabric lining, an EVA insole, a side gore panel, and a heel pull tab make it easy to slip on and off. It sits at ankle height on a rubber outsole, which makes it a neater choice than a tall rain boot.

Wear it with black leggings, a hooded rain jacket, and a crossbody bag on stormy mornings. It also works with cropped straight jeans and a chunky knit when the forecast looks iffy. Keep it by the door next to the chestnut UGG Classic Mini II and you have dry days and cozy days covered.

Skip it if: Skip it if you want a boot that works for the office.

Shop it at Zappos

What ankle boots are best for walking all day?

Look for a low, wide heel, a cushioned footbed, and a rubber or lug sole. The Blundstone Classic 585 and both Cole Haan Fenella boots earn a 5 for walkability on our list. Skip leather soles and heels over 3 inches if you will be on your feet for hours.

What are the best ankle boots for women in wet weather?

Choose a pair the brand describes as waterproof, not just water resistant. The Sorel Chelsea rain boot, both Cole Haan Fenella boots, and the Dolce Vita Soline H2O all list waterproof construction. Water resistant pairs like the Blundstone and the UGG Classic Mini II handle light drizzle, but they are not made for standing in puddles.

What should I wear with ankle boots?

Straight and cropped jeans that end at or just above the boot are the easiest match. Flared or wide leg pants look best over a heeled bootie, so only the toe shows. With dresses and skirts, try opaque tights in a shade close to the boot for a long, unbroken line.