Women’s Ankle Boots that are Actually Comfy

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 can eliminate 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, 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 bootcut 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 weatherproofing balm before wearing them.

Available from Amazon

Blondo is a Canadian heritage brand that I love for the comfort of its designs. I have a pair of 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 Amazon

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 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

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

Available from DSW.com

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 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 comfortable right out of the box with little to no break-in time. This is casual, lightweight, suitable for work, and great with a pants design that you can walk all day in.

Available from Amazon

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 hurts 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. Other women find this style 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 is always a safe option if you want 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 look professional 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 is comfortable enough to wear all day.

Available from Amazon.com

The Dansko Maria is an interesting bootie that will either work with your foot shape or not. Those who love this style like it, but it won’t necessarily fit all women’s feet well. If they fit you, 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 cute option for everyday wear. They do have 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’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 good tread and grip for wet conditions. They have excellent arch support while still looking look cute and stylish.

Available from Amazon.com

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 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 you can wear if you have foot issues.
The Vionic Cecily is one design that is both fashionable and has the proper amount of support and cushioning, so they are good for those women who are dealing with foot pain. Vionic styles, in general, are roomier than other brands, have good arch support, and have firmer soles.

Available from Vionic

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 cold because of the split ankle detail.

Available from Nordstrom

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