16 Women’s Ankle Boots and Booties that are Actually Comfy

Booties and ankle boots are a popular not only because they are 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 booties to choose from, so we have narrowed it down and come up with a list of the most comfortable ankles boots that are available.  Our choices are all beautiful and dependable everyday boots 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 Boot

The Lucky Brand Women’s Basel Boot is a best selling leather bootie 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 a good height for walking. The boot 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 easily 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 weather proofing 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 boots. I have a pair of their no 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 is 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 these boots 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 boots that are waterproof, so that and the insulation make this a stylish winter boot that is worth a look. Overall this is a great boot 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 Ankle Boot

The Teva Women’s Foxy Ankle Boot are a good option if you are looking for an all around durable, yet 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 Deia Bootie

The Toms Deia Bootie is a nice, simple style that comes in a good variety of basic colors.The bootie is made of 2 fabrics, suede and wool, so it gives it an interesting look that you can dress up or down. The heel is approximately 1 ¼”,  so it isn’t too high or too low, and the boot opening is 10.5 inches which is also fairly average.They are easy to get on and off with a little help from a suede pull tab at the back of the heel, as well as an elastic fabric panel that is in the shoe. You can’t see it in the picture, but there is also a zipper on the inner side of the design.  As far as comfort goes, that elastic fabric panel also helps to provide stretch that accommodates the shape of the foot, making it feel a little more comfortable. This shoe runs a bit small and narrow, so if you have a wider foot, you may want to buy a half size up. They are suede, which while it helps to make them feel soft and comfy, it may make them difficult to wear in wet conditions unless you spray them with a waterproofing spray. The Deia 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

CLARKS Women’s Sillian Sway Ankle Bootie

The Clarks Sillian Sway Ankle Bootie are a great option for those who have mobility issues and have difficulty putting on boots with side zippers. This is an interesting 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 boot opening is approximately 11″ around. The Sillian Sway have 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 causal, comfortable, light-weight, suitable for work, great with 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 boot in the leather version of this design and was a little surprised that a lot of women find it to be a comfortable style. 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 in 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 everyday, 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 are always a safe option if you are looking for a comfort 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 nice 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 Nordstrom

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 love it but it won’t necessarily fit all women’s feet well. Despite the kind of bulky look to them, they are actually quite a simple design and  are deceptively lightweight. Their unique style and nice 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 Collection Cobb Hill Nicole

Rockport’s Nicole are a cute, short boot that is great for all day wear. They have some interesting detailing including a ruched vamp and antiqued rivets on the heel strap. Since they are Rockport, you know they will contain Rockport’s traditional comfort technology and comfort soles. The sole on the Nicole 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 great arch support, while still looking look cute and stylish.

Available from Rockport

Born Kerri

 

Born are one of those brands that a lot of people really love for comfort and durability. One of their most popular boots is the Born Kerri. They are very comfortable, super stylish, and have a great cushioned footbed. Born sizing is often a little bit off for some reason, so if you do choose to check out this boot 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 Faros

VIONIC are a brand that are known to make great shoes for people who have plantar fasciitis or other issue that cause foot pain. It can be hard to find cute styles that you can wear if you have foot issues. The Vionic Faros is one design that is both fashionable and has a good 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, a fringe and some studs along the shaft. Vionics in general are roomier than other brands, have good arch support, and have firmer soles.

Available from Amazon

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. UGG boots 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

Frye Reina Bootie

The Reina Bootie are a much loved, high heeled bootie. They are a little bit country, a little bit rock and roll, and a whole lot of sexy. Despite the high heel, this style manages to maintain its comfort according to a lot of women who own this boot. Like most Frye boots, it is also very well made and the leather is high quality and super soft.  These boots are able to elongate the look of your legs, making them work well with dresses, leggings or skinny jeans. Because the leather is super soft they are comfortable right out of the box with no breaking in required. The leather has a fairly distressed look to them, but that only adds to their versatility.

Available from Zappos

Everlane The Boss Boot

Everlane’s The Boss Boot are a really nice, super modern style that still manages to be comfortable enough to walk long distance.  They have a fashionable 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 boot is high quality and stylish. Currently they only come black and the burgundy, but both colors are beautiful in person.

Available from Everlane

RAG & BONE Harrow’ Leather Boot

The Rag & Bone Harrow’ Leather Boot is a cap-toe high heeled (3 inch!) bootie. It has a leather upper with a shearling lining, so you can wear it in cold weather but since the heels are so high and the soles don’t have a lot of grip they aren’t a good option for ice and snow. Despite the high heel, 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 a one of the most versatile, comfortable, and fashionable high heeled boots going.

Available from Nordstrom

Seychelles Snare

 

If you have a narrower foot, the Seychelles Snares may be a good option for you. They are made from a flexible, soft leather so they are soft and comfy to wear . The design is a little different with the  split ankle detail with a super short zipper, which it makes it look really cute, but it may show your socks since it is so low. The Seychelles Snares comes in some really nice and unique colors and the leather is pretty high quality. The only downside to this style is the boot opening is a little wide and the ankle flaps may lose their shape and flop over, which some women like and some not so much.

Available from Zappos

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