Women’s Ankle Boots that are Actually Comfy

Eleven of the most comfortable women's ankle booties in various shades of brown, gray, and black

If you want to give your feet some love but keep things super stylish, you can’t go wrong with a pair of comfortable ankle boots for women. The best styles can be excellent wardrobe staples that stay fashionable year after year, and if you get the right pair will leave your feet feeling great.

It isn’t hard to find pairs that are the perfect combo of fashion and function that you can wear for walking all day or for exploring when you travel that just happens to be good for your feet. With comfort features like cushioned footbeds, sturdy soles with shock absorption, and arch support, you won’t have to worry about aching arches and sore soles. We have found styles you will love wearing, from comfortable podiatrist-approved low stacked heels to chunky-heeled wedges that give a bit of height.

You can wear these booties from the start of fall and possibly right through winter, depending on where you live.
Another bonus is they’re easy for everyone to pull off since they look great with skinny pants, leggings, skirts, or dresses, whether for work or in your off hours on the weekend.

There are so many boots to choose from, so we have narrowed it down and come up with a list of the most comfortable ankle boots available for women. Our choices include the best ankle boots based on outstanding reputations for comfort as recommended by podiatrists, fashion experts, and thousands of glowing reviews from real women.

Read More: 14 Comfortable and Warm Women’s Winter Boots

Lucky Brand Women’s Basel

Lucky Brand Women's Basel

The Lucky Brand Women’s Basel is a best-selling leather style with a rubber sole. The rubber sole makes them easy to walk in because they help with shock absorption and eliminating pain. The heel is 1.5 inches, and it has a slight platform of 0.25 inches, which is also the right height for walking. The opening is on the smaller side at only 10 inches around, so there isn’t much of a gap between your ankle and the boot like there can be with some of the other styles, but most women find the fit to be pretty good. However, it is generally recommended to size up 1/2 a size with the Basel since they fit a little small.

The leather is very soft, with a buttery feel to it, which helps add to the comfort level. They are stylish yet simple, so you can comfortably wear the Basel with dresses, skinny jeans, or even boot cut jeans. They don’t tend to do all that well in wet weather (the leather seems to become discolored), so if you go for this design, you will want to treat them with some weatherproofing balm before wearing them.

Available from Amazon

Blondo Villa Waterproof

Blondo Villa Waterproof

Blondo is a Canadian heritage brand that I really love for the comfort of their designs. I have a pair of their low heeled booties that they don’t seem to sell anymore.

One of their designs that is super similar to the ubiquitous Sam Edelman Petty but is waterproof and has an insulated lining is the Blondo Villa Waterproof. The other differences between this style and the Petty are that the heel on the Villa is slightly higher, the shaft is slightly taller, and the ankle is narrower. The sole also has much more grip so that you can wear this footwear in the worst weather conditions, and you won’t have to worry about slipping or wrecking the leather or suede.  It is pretty unusual to find waterproof suede styles, so that and the insulation make this a stylish winter boot that is worth a look.

Overall this is a great option for walking in the winter as it has enough tread on the bottom to deal with wet and icy conditions. They are also comfortable enough to wear for walking long distances.

Available from Zappos

Teva Women’s Foxy

Teva Women's Foxy

The Teva Women’s Foxy is a good option if you are looking for an all-around durable yet comfy style that is excellent as an everyday boot that will leave your feet feeling great. They may have a slight breaking in period, but you will love the comfort that this style provides once broken in.

The Foxy Ankle has a round toe that is somewhat roomy and will give your toes a little bit of space. They hold up well to harsh conditions, and the rubber sole means that they are great for walking in. They are made from Nubuck leather, and the heel is approximately 2″, so it has a little bit of height. The Foxy Ankle has a removable comfort insole, in case you need to add orthotic insoles. They are easy to clean with a damp cloth and seem to be waterproof. The boot opening measures approximately 10″ around.

Available from Amazon.com

Toms Kala

Toms Kala

The Toms Kala is a nice wedge style that comes in a good variety of basic colors. The bootie is made of suede leather that gives it an interesting look that you can dress up or down. The heel is approximately 2 3/4”,  so it gives a decent amount of height.

As far as comfort goes, the Kala is known for being surprisingly comfortable, especially for a wedge style. Since they are suede, they have a nice soft feel to them, making them difficult to wear in wet conditions unless you spray them with a waterproofing spray. The Kala is a cute style that goes well with any outfit, and it has enough cushioning for wearing all day, walking long distances, or for travel.

Available from Zappos.com

CLARKS Women’s Sillian Sway Ankle Bootie

CLARKS Women's Sillian Sway Ankle Bootie

The Clarks Sillian Sway Ankle Bootie is a great option for those who have mobility issues and have difficulty putting on styles with side zippers. It is a useful design because it has Velcro closures on both sides, so you can easily reach down and pull the Velcro open, slide your foot in, and then close the Velcro. They are extremely cushioned because they have the “Cloud Steppers” insoles. The sole has a slight platform of .5 inches, while the heel is inches 1.35 inches.

If you are looking for a style to accommodate larger ankles, this may be a good option as the opening is approximately 11″ around. The Sillian Sway has the usual Clarks quality, so they are pretty comfortable right out of the box with little to no break-in time. Overall, this is a casual, lightweight, suitable for work, great with a pants design that you can walk all day in.

Available from Amazon

Sam Edelman Petty

Sam Edelman Petty

 

The Sam Edelman Petty is one of the most popular booties on the market. I own this style in the leather version of this design and was a little surprised that a lot of women find it to be a comfortable option. For me, the toe box is a little too narrow, and it ends up hurting the top end of my feet when I wear it for any length of time and have to do some walking. My feet are a little wide, and this is quite a narrow design, but other people who have wide feet seem to find that the leather stretches enough to make them comfortable. Regardless, other women find this style to be very comfortable, so it is on the list.

The features that women love about the Petty are that the shaft is pretty short, the moderate heel height (1.5″) is good for every day, and the look of the wooden sole is very nice. These are easy to clean and are very well made.  They come in a suede or leather upper, and they have a side zipper.

Available from Amazon

Naturalizer Cassandra

Naturalizer Cassandra

Naturalizer is always a safe option if you are looking for a comfortable style. A bootie that they make that is comfy and stylish is the Cassandra. It has crossed buckle straps to give it a bit of subtle detailing. It has only a slight 1.24-inch heel,  as well as a contoured dual-density foam footbed, so it is a good option if you have to do a lot of walking.

The Cassandra can be worn with jeans or a dress and are professional looking enough for an office environment. You can’t see it in the picture, but they also have a side zip. Overall the Cassandra offers good quality, great fit, and are comfortable enough to wear all day.

Available from Zappos.com

Dansko Maria

 

Dansko Maria

The Dansko Maria is an interesting bootie that will either work with your foot shape or not. Those who love this style really like it, but it won’t necessarily fit all women’s feet well. If they fit you, then they are also very comfortable and don’t require a break-in period.

Despite the kind of bulky look to them, they are quite a simple design and are deceptively lightweight. Their unique style and beautiful color make this a really cute option for everyday wear. They do have kind of a Dansko clog look to them, but surprisingly they don’t make a clomping clog sound when you walk. Dansko boots are often highly recommended by podiatrists because they have a great reputation for making shoes that are good for your feet.

Available from Zappos

Rockport Cobb Hill Alexandra

Rockport Cobb Hill Alexandra

Rockport’s Cobb Hill Alexandra is a cute, short boot that is great for all-day wear. The Alexandra has some interesting detailing, including a ruched vamp and antiqued rivets on the strap. Since they are Rockport, you know they will contain Rockport’s traditional comfort technology and comfort soles.

The Alexandra’s sole is rubber, which means they are going to be comfortable for walking and will have a good tread and grip for wet conditions. They have excellent arch support while still looking look cute and stylish.

Available from Zappos.com

Born Kerri

Born Kerri

 

Born are one of those brands that a lot of people love for comfort and durability. One of their most popular boots is the Born Kerri. They are very comfortable, super stylish, and have a significantly cushioned footbed.

Born sizing is often a little bit off for some reason, so if you choose to check out this style, you may want to go a half-size down, but check sizing recommendations if you are buying online.

Some women mention this isn’t the best option if you are doing a lot of walking, but they are comfy if you are just wearing them for the office or for outings that don’t involve much walking.

Available from Zappos

Vionic Raina


VIONIC is a brand known to make great shoes for people who have plantar fasciitis or other issues that cause foot pain. It can be hard to find cute styles that you can wear if you have foot issues.

The Vionic Raina is one design that is both fashionable and is podiatrist approved with the APMA Seal of Acceptance so you can rest assured that this design has the proper amount of support and cushioning, so they are good for those women who are dealing with foot pain. They have nice detailing, including a little tassel on the zip. Vionic styles, in general, are roomier than other brands, have good arch support, and have firmer soles.

Available from Vionic

UGG® McKay Water Resistant Bootie

UGG® McKay Water Resistant Bootie

The UGG® McKay is a water-resistant, sheepskin bootie with a nice shorter shafted version of the ubiquitous UGG classic boots. This style is great for comfort because it is lined with genuine shearling. The Treadlite sole means you can wear it in slippery conditions, although you probably aren’t going to wear this design out in wet slushy weather as it would ruin the sheepskin.  It has a very low 1″ heel, and it is a pull-on style. Some women find them a little hard to get off and on.

Like most UGG styles, it is comfortable, well made with good cushioning, and durable soles. UGGs do stretch a little to your feet, so don’t panic if they feel a little tight when you first try them on. The only downside to this style is that if you wear them without socks in cold weather, your ankles will feel the cold because of the split ankle detail.

Available from Nordstrom

Felicia Wedge Bootie

Felicia Wedge Bootie

The Felicia is a much-loved wedge bootie/sneaker from Linea Paolo. According to many women who own this style, the wedge heel helps this style maintain its comfort. The Felicia comes in a fantastic selection of different colors of high-quality leather. Because the leather is super soft, they are comfortable right out of the box with no breaking in required. They have a side zipper closure for easy on and off, and the rubber sole is skid resistant.

Available from Nordstrom

Everlane The Boss Boot

Everlane The Boss Boot

Everlane’s The Boss Boot is a beautiful, super modern style that still manages to be comfortable enough to walk a long distance.  They have a chic pointed toe, which makes them dressy for work or nights out, but they can also work with casual styles. These boots give enough of a height boost to elongate your legs without being uncomfortable to walk in. Everything about this design is of high quality and stylish. Currently, they only come in black, bone, and snakeskin.

Available from Everlane

Keaton Water Resistant Lace-Up Bootie

Keaton Water Resistant Lace-Up Bootie

The Keaton Water Resistant Lace-Up Bootie is a cute utilitarian bootie. It has a leather upper and lining, so it is good for moderate weather and can even handle a little rough weather due to the rubber gripped sole. Most women find this style to be comfortable partly because the leather stretches out nicely, and they end up molding to your feet. It is one of the most versatile, comfortable, and fashionable boots going.

Available from Nordstrom

Sources:
American Podiatric Medical Association (APMA) APMA.org

Molly London
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