16 Women’s Ankle Boots that are Actually Comfortable to Wear

Ankle booties are popular because they are not only fashionable and look great with skinny jeans or dresses, but also because many brands are putting out styles that are great for walking and wearing for travel. There are a lot of short boots to choose from, so we have narrowed it down and come up with a list of the most comfortable styles that are available.  Our choices are all beautiful and dependable everyday booties that are great for wearing with skinny pants, leggings, and skirts.

Read More: 15 Comfortable and Warm Women’s Winter Boots

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. Although 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 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 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 suede styles that are waterproof, 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

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

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 but it makes 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

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 inch, 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, comfortable, light-weight, suitable for work, great with a pants design that you can walk all day in.

Available from Amazon

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 Zappos

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. These 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


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. 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. If they fit you, then they are also very comfortable and don’t require a break in period. They do have kind of a Dansko clog look to them, but surprisingly they don’t make a clomping clog sound when you walk.

Available from Zappos

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 sole on the Alexandra 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 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 do 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 is a brand that is 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 Serena is one design that is both fashionable and has the right 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

The UGG® McKay is a water-resistant, sheepskin bootie that is 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

The Felicia is a much-loved, wedge bootie/sneaker from Linea Paolo. The wedge heel helps this style to maintain its comfort according to a lot of women who own this style.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’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 a dressy for work or nights out, but 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 black, bone, and snakeskin.

Available from Everlane

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

Seychelles Floodplain Block Heel Bootie


If you have a narrower foot, the Seychelles Floodplain may be a good option for you. They are made from flexible, soft leather, so they are soft and comfy to wear. What I love about this bootie is that you can get it in leopard print or a brown crocodile print which look very fashionable and chic.

Available from Nordstrom

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