That’s why we’ve put together a list of our favorite boots that are truly comfortable and supportive (yes, that means no break-in period, easy to walk in, and perfect for all kinds of activities!). From the best winter boots to the best hiking boots, keep reading to find the pairs we’d wear straight out of the box—and keep on for life.
What to consider:
Size/Width
Adenike Sonaike, DPM, podiatrist and medical director of Baker Street Health says it’s crucial to pay attention to shoe size (and whether a brand is true-to-fit) and width (narrow, medium, wide, extra wide). “The right size and fit of your boot will prevent pinching at the toes, microtrauma from your toes stubbing the front end of the shoe, and instability from your ankle moving from side to side in a boot that’s too large/wide.”
If you’re going for a pair of taller boots, keep calf size in mind to make sure they’ll fit comfortably around your legs. The only knee-high options on this list is the Reformation and Bootbarn pairs, and after testing, we can confirm they’re super roomy for muscular calves but structured enough to stay snug on slimmer ones too.
Material
All the below boots are made from different materials—some are waterproof, others are leather, and the list goes on. “But, any boot you buy should provide a sturdy material around the ankle,” says Sonaike. “If you have a history of weak ankles, avoid materials with excess elastic fabric, which prevent stability due to increased flexibility,” she says. We curated this list to ensure every option provided proper ankle support, regardless of fabric.
Heel and fabric height
Sonaike describes “fabric height” as how high the boot extends up your leg. “An ankle boot that continues above the ankle versus stopping under the ankle will boast more comfort and stability, as it supports your ankle ligaments and can help prevent injuries such as ankle sprains.” In simple terms, if a boot covers your ankle, it’ll be way more comfortable and supportive.
And, speaking of ankle support, you’re going to need more of it when opting for a boot with a higher heel to make the shoe feel more comfortable. Additionally, when shopping for a higher heel, make sure it’s a thicker one like a block heel or wedges. And, Sonaike says double check that your toes are not sliding forward and hitting the front of the shoe with a higher heel. “This will cause toe pain and toenail pain in the long run.”
How we chose
As a style writer who’s been putting shoes through the paces for years, I’ve tested tons of comfortable boots: The options with the most support made it onto this list. I also consulted a podiatrist to get pro-level intel on comfortable boots. She emphasized that the fit, material, and heel height of a boot are things to look out for when shopping. WH fitness and commerce editor Nicolette Accardi, and WH fashion director Kristen Saladino also weighed in.
So, are you ready to find the most comfortable boot of your life? Look no further than the below tried-and-tested list.
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Vagabond is known for delivering everyday comfort and support, says Sonaike, and these shoes are at the top of our list. Why? They’re made with incredibly supple leather (more on that later), feature a square toe box, and have a higher block heel that adds height without sacrificing walkability. Plus, they hit above the ankle for added support (this helps to prevent injuries like sprains!).
The Dorahs are also one of the most versatile boots on our list—they go with just about any outfit, but they can also support your feet for miles on end without a wince of pain. They have a super comfortable footbed that literally feels like a cradle for your arches, and the soft leather upper holds the foot in place and ensures it’s not moving around while you walk. I also love the elastic side panels, which make the shoes super easy to pull on.
Another pro? Unlike many leather boots we’ve tried, these don’t require any breaking in. In our experience, they were wearable straight out of the box, with no signs of poking or pinching in sight. While they may feel a bit snug at first, stretching them out a bit only takes a few quick wears in our experience.
They are definitely on the pricier side, but the quality of the leather, their durability, and the fact that they match with everything makes them well worth the pretty penny in our book.
Read More: Best Walking Shoes For Women
| Sizes | 5-12 |
|---|---|
| Colors | 2 |
| Material | Leather |
| Fit | Regular |
| Comfort Features | Soft leather, square toe box, high block heel, ankle support |
Pros
- Very roomy toe box
- Wide in the calf area, but still structured if you have a slimmer leg
- 70s, vintage-y vibe
Cons
- Run a full size too big
I was a little skeptical when I first got these Reformation boots, wondering if the structured toebox would fit my wider feet. But as soon as I slipped them on, I was pleasantly surprised—there was plenty of room. I took them out for a night on the town, and they were even better than I expected. No awkward pinching or heel pain, which is rare for new boots that usually need breaking in. These were comfortable right from the start.
I would recommend sizing a half size to a full size down, as my typical 9.5 size was a bit large on my foot. I wish I bought a 9, but I just added a heel pad to the insole to keep my foot in place and it works like a charm.
I wore these boots all through the summer with shorts and skirts, and have now been rocking them in the colder weather with jeans or trousers—they literally go with everything. And, I love the 70s-esque design of them. The square toe and block heel add the perfect touch of funky to any outfit.
When I first got the boots, I wasn’t sure about the look—they just seemed too new, like they needed that lived-in vibe. But after wearing them a few times, they started to break in beautifully. The leather softened up, giving them that perfect vintage look and feel I’d been searching for.
| Sizes | 5-11 |
|---|---|
| Colors | 3 |
| Material | Leather |
| Fit | Wide |
| Comfort Features | Block heel, wide toe box, soft leather |
Despite the fact that this boot looks (and feels!) like the chicest sock you’ve ever seen, its fabric is surprisingly supportive around your ankles. The kicks feature a stretchy knit upper, a roomy square toe, a pull tag on the back of the shoe, and a block heel for stability and extra support. Plus, the insole has double (!!) arch support, which makes the shoe feel super cushy and it also relieves any pressure, so you can finally wave g-bye to pain while wearing heels. Finding a heel you can walk miles in is tough, but this one pulls it off—and then some.
This shoe is also water-repellent (I know, it doesn’t look like it!). I also love that the shoe has a rubber outsole, which keeps me feeling secure on slippery pavement. After testing many pairs of shoes over the years, we agree that finding a pair of waterproof heels that are *actually* cute is a rarity, which is why these are so coveted in our collection.
Made with 100 percent recycled plastic water bottles, the boots are super easy to slip on and never require tugging or pulling to get off. And, the array of color choices took us by surprise—we’ve never seen a boot that comes in 17 different colorways.
If you’re looking for a pair of boots to wear out with the girls, but don’t want to compromise on foot support, these extremely versatile and comfy heels are where to go.
| Sizes | 5-11 |
|---|---|
| Colors | 17 |
| Material | Recycled plastic |
| Fit | Narrow-regular |
| Comfort Features | Stretchy upper, roomy toe box, cushioned insole, block heel, pull tabs, waterproof |
Pros
- Keep the feet super warm
- Rubber outsole helps with traction
- Insole offers superior shock absorption and support
Cons
- Wish the boots came in a few different colors
I’m not gonna lie, there are some of the cutest winter boots I’ve ever seen, and WH fashion director Kristen Saladino agrees. “Not only are they super chic for being winter boots (which aren’t always the cutest) but they’re perfect for sloppy winter days or ski weekends away,” she says. These boots have the style of a sneaker with the functionality of a boot, but without the usual clunky, heavy feel. They’re surprisingly lightweight and super easy to walk in—more like wearing a sneaker than your typical snow boot.
These winter boots are designed with waterproof protection, which is a saving grace when you’re trekking through snow, wet grass, puddles, and the list goes on. The rubber outsole helps in these conditions, too.
And, of course, they wouldn’t have made it onto this list if they weren’t super comfortable. The features to write home about? A removable EVA footbed, which is an insole that offers great shock absorption and support, as well as a molded rubber insole to protect and hold the foot in place. And, you never have to worry about them being hard to take off, as they have heel pull tabs that make the shoe *so* easy to slide in and out of. Lastly, when things get super cold, the shoes feature faux fur that keeps the feet cozy and warm.
They come in two different colors, too—one more neutral and one that has fun shades of red and blue. However, we do wish that there were a few other, more neutral colors to choose from.
Read More: Best Winter Boots
| Sizes | 6-11 |
|---|---|
| Colors | 2 |
| Material | Nylon, leather, suede |
| Fit | Regular |
| Comfort Features | Removable EVA footbed, rubber insole, pull tabs, faux fur for warmth |
Pros
- Not super clunky
- Cushioned insole feels super comfortable
- Super insulated
Cons
- Wish they came in half sizes
Speaking of waterproof, let me introduce you to my all-time favorite pair of rainboots from Hunter, a brand known for having tons of different styles of stylish waterproof boots. This pair in particular sits at ankle height, so they don’t feel super clunky, but they’re tall enough to keep rain out and your feet and ankles totally protected.
The boot also comes suited with a lugged sole for extra traction on slippery terrain. And, I love the addition of neoprene at the top of the boots, which offers some serious insulation, making them great for colder days (I will admit, I wear them in the snow all the time). The addition of loops at the front and back of the shoe makes them even easier to pop into.
As far as comfort goes, these boots have a roomy toe box and a cushioned insole to make your feet feel nothing but secure and comfortable. I can seriously walk miles in them, and I don’t say that about a lot of styles I own. I do wish they came in half sizes, though. I had to size up, and they feel just a little too big.
| Sizes | 5-11 |
|---|---|
| Colors | 3 |
| Material | Rubber, neoprene |
| Fit | Regular |
| Comfort Features | Lugged sole, pull loops, roomy toe box, cushioned insole |
Pros
- Come in regular and wide sizing
- Superb ankle support
- Offer solid under-foot protection
Cons
- Require some breaking-in
The Oboz Sawtooth X Mid is our winner for our all-time favorite hiking boot, and there’s no questioning why. They put up a good fight in wet weather conditions (hi, snow and rain), they have a nylon shank, which is a piece of material between the insole and outsole that offers solid underfoot protection and helps you stay balanced on all terrains. Plus, they have rubber outsoles for stability on every surface, including rocks and gravel.
These boots don’t have a ton of give, so they do actually require some break-in time. However, we find that to be the case with most high-quality hiking boots. If you’re setting off on a hiking trip, we recommend wearing them on a few long walks or hikes beforehand so they’re primed and prepped for your excursion.
We’re also big fans of the ankle support these hikers offer. Since they go up to the ankle, there’s no slipping or rolling, and your foot and lower leg feel secure the entire hike.
Bonus: They come in both regular and wide sizes, so if you’ve got wider feet or bunions, you’re covered. Don’t these sound like the best hiking boots ever? Trust us—they totally are.
| Sizes | 5-12 |
|---|---|
| Colors | 4 |
| Material | Leather, mesh |
| Fit | Regular, wide |
| Comfort Features | Nylon shank, rubber outsole, wide sizes, waterproof |
Pros
- Great for those with wide feet and bunions
- No break-in time
- Super comfortable to walk in
Cons
- Can be slippery on certain surfaces
There are several great leather boots on this list, but WH fitness and commerce editor Nicolette Accardi calls these her all-time favorite. They’re elegant and have that “cool girl” vibe, plus they require no break-in time—a rare find for leather boots! “It typically takes me at least four weeks to break in a pair of leather boots, but the Genny Boots morphed to my feet after just one wear,” she says.
And, as someone who averages over six miles of walking per day, these have never given her pain. She says the block heel makes the shoe feel super comfortable, as it offers more support than a skinnier heel, which historically makes her feet feel wobbly.
Her only con? The sole can be slippery when walking over certain surfaces. She wishes there was more traction on the bottom of the shoe.
| Sizes | 5-11 |
|---|---|
| Colors | 3 |
| Material | Leather |
| Fit | Wide |
| Comfort Features | Soft leather, block heel |
Pros
- Comes in a wide foot and wide calf option
- Super comfortable for walking
- Square shape offers room at the front of the boot
Cons
- Feels tight around the foot for the first few wears
I’d been searching for a cute pair of cowboy boots for about a year before I found these. With wider feet, I really wanted a pointed-toe style that wouldn’t pinch. Luckily, a friend with the same issue got these boots first and said they were super comfortable, needed no break-in time, and fit wide feet perfectly. After getting them myself, I truly couldn’t agree more.
First off, these boots are made with full-grain leather, giving them a super soft and flexible feel. I love that I didn’t have to break them in like most leather boots—I walked to dinner and back without feeling a single pinch. That said, they do feel a bit snug at first, especially around the foot. It loosens up over time, but the first few wears can make them tough to take off. Now, they slip off like a dream. It’s worth mentioning that the leather needs some time to soften around the heel (but don’t worry—these boots never hurt, just tricky to take off at first). Luckily, the pull tabs make it easier.
Another plus? This boot comes in a wide foot and wide calf option, which we recommend buying if you typically opt for a wider boot. I went with a regular and it fit perfectly around my calves and even my wider feet, but my friend has the wide calf option and says it’s perfect for her strong legs.
The comfort of these boots comes in a few places. They have a cushioned insole, which supports your feet if you’re out and about all day, and a lower heel which offers that cowboy-esque touch without compromising on comfort. These boots also have a snip toe design, meaning the toe is slightly pointy but also a little square. The square shape gives more room at the front compared to pointy boots, which I really appreciate for my wider feet.
| Sizes | 6-11 |
|---|---|
| Colors | 2 |
| Material | Leather |
| Fit | Regular, wide |
| Comfort Features | Cushioned insole, lower heel |
Lily Wohlner is the Associate E-Commerce Editor of Women’s Health. An expert in recommending the best products to add-to-cart, she knows what it takes for a product to receive a solid five stars (especially when it comes to beauty!). Starting her career as a freelance makeup artist, Lily has since moved to the editorial world, where she has generated content for brands including Oribe, NewBeauty, Dermstore, SkinStore, and LOOKFANTASTIC. When she’s not zenning out with a pore-clearing mask, the Lower East Side dweller is cheffing up a new recipe with her roommate or thrifting for the perfect pair of blue jeans. Follow her on Instagram.
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