We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (2024)

We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (1)

Dressing for the weather is crucial in any season, and when chilly temperatures or rainy forecasts hit, you'll want to be prepared with proper footwear. Your boots should not only stand up to the elements and enhance your ensemble but also keep you comfy while out and about.

According to podiatrist and foot surgeon Mona Ramani, DPM, the most important features of a comfortable boot are a good shaft width, a modest heel height, and a roomy toe box. She says the latter should be "wide enough to prevent crowding of your toes."

Sometimes you never know if a pair of shoes will be comfortable or not until you try it out. We tested 93 pairs of shoes firsthand to find the most comfortable ones, evaluating each style for comfort, support, fit, durability, quality, and value. After an ongoing testing period of six months, we narrowed it down to 11 pairs of the most comfortable women's boots.

Our Top Picks

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We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (2)

Our Ratings

  • Comfort

    5/5

  • Durability

    5/5

  • Value

    5/5

  • Fit

    5/5

Why We Love It

  • These high-quality, stylishly versatile boots are comfortable on the first wear and handle inclement weather like a champ.

What to Consider

  • Each shoe weighs more than a pound, so keep that in mind when packing.

Earning perfect scores in all testing categories, the Blondo Danika Bootie is our No. 1 pick. Like all styles from the brand, this pair is crafted from durable leather and features a waterproof coating and water-sealed seams. These boots are easy to slip on, true to size, and comfy on the very first wear, and they kept our feet happy while jaunting around Quebec City and Montreal.

That said, you'll want to wear taller socks to prevent them from slipping down and causing uncomfortable rubbing. Also, each shoe weighs more than a pound, so keep that in mind when packing. The versatile design goes well with leggings and a knit sweater during the day and can be dressed up for dinner and drinks at night. We wouldn't necessarily call these booties budget-friendly, but we think the price is reasonable considering how comfortable, stylish, and well-made they are.

The Details: Sizes 5.5 to 11 | Leather or nubuck

We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (3)

Our Ratings

  • Comfort

    5/5

  • Durability

    5/5

  • Value

    5/5

  • Fit

    4.5/5

With Marc Fisher's Yale Booties, you don't have to sacrifice style for comfort. The pointy-toe, slightly heeled style fits true to size. Our only complaint was that the shaft opening is somewhat wide, but this is mostly a matter of preference and will ultimately depend on what you wear them with. We're big fans of the rich color, angled mesh panels, and subtle metallic hardware. You can truly pair them with just about everything, from leather to knit. While the price is a bit steep, they're definitely more comfortable, sturdier, and better-made than other options.

The Details: Sizes 5 to 12 | Leather

We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (4)

Our Ratings

  • Comfort

    3.5/5

  • Durability

    4/5

  • Value

    4.3/5

  • Fit

    5/5

Why We Love It

  • These waterproof boots are well-constructed and surprisingly sturdy, with a simple silhouette suitable for various occasions.

What to Consider

  • They run slightly narrow and may not work for people with wide feet.

Looking for durable winter shoes that don't break the bank? The Asgard Ankle Boots might be your best bet. The Chelsea-style design is well-constructed and fits true to size, albeit somewhat narrow. Both the outsoles and uppers are rubber, offering waterproof protection in wet or slushy conditions. While we found these boots comfortable, they're not very cushioned and may not be ideal for all-day wear, especially on heavy-walking days. Still, they make excellent rain boots, and the simple silhouette is versatile enough to rock on various occasions. And you really can't beat the price.

The Details: Sizes 4 to 12 | Rubber

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Why We Love It

  • Featuring plush shearling linings, these cute and comfy Uggs make you feel like you're walking on clouds.

What to Consider

  • They only come in whole sizes and run slightly small.

It should come as no surprise that Ugg makes our favorite shearling boots. We rocked the Classic Short II all around town, while on pavement, stepping in grass, with socks, without socks, with bare legs — you name it. Wearing them is like walking on clouds, and there's zero break-in period. They're pre-treated to repel water, and you can coat the suede periodically with a water-resistant spray to preserve the material.

One thing to note is that Uggs only come in whole sizes, and this pair runs slightly small, so you may want to size up if you're in between. But either way, they're ultra-soft and stretch over time, so you won't have to worry about blisters or foot pain. These cute and comfy boots are a stellar choice for travel days, running errands, spending time at a ski lodge, or just hanging out in chilly weather.

The Details: Sizes 5 to 12 | Suede, shearling

Why We Love It

  • These trail-ready boots provide arch support, ankle protection, traction, and waterproof protection from puddles.

What to Consider

  • They aren't as stylish as other pairs we tested.

The Hi-Tec Altitude Boots fit as expected, leaving just enough wiggle room for thick socks. There was no break-in period, so we were ready to hit the trails on the first wear. The cushioned insoles supported our feet, the sturdy shafts protected our ankles, and the tractioned outsoles prevented slips. Meanwhile, the waterproof design kept our feet dry when stepping directly into deep puddles. The exteriors dried quickly, too. These boots are heavy but not so much that they'll hold you back on a hike, and they seem super durable. This isn't the most fashion-forward pair we tested, but it serves its purpose as a comfortable, supportive trail shoe.

The Details: Sizes 6 to 11 | Leather

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (9)

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (10)

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (11)

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (12)

Why We Love It

  • These boots will keep your feet reliably dry while helping prevent slips, and the durable rubber design is made to last.

What to Consider

  • They're only available in whole sizes and run slightly large.

Bogs makes our favorite rain boots. This durable rubber pair carried us through the rainy season in Vermont, including a period of flooding. We wore them while running errands, walking on slick store floors, trudging through wet sports fields, across gravel, and on various other outdoor terrains — and they kept our feet not only reliably dry but also comfortable. They have great traction, too, which helps prevent slips.

These boots are easy to get on and off, thanks to the heel tabs and stretchy gore panels, and they were comfy the first time we pulled them on. The thick rubber seems like it'll hold up for years, and it's definitely not too heavy. We also like the cute, versatile style. Just a heads up: they only come in whole sizes, and we found that they run a smidge large.

The Details: Sizes 6 to 11 | Rubber

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Our Ratings

  • Support

    5/5

  • Durability

    5/5

  • Value

    5/5

  • Fit

    5/5

Why We Love It

  • These Uggs are comfy on the first wear, not to mention lightweight, durable, waterproof, and exceptionally warm.

What to Consider

  • Sizes 10 and above don't come in half sizes, and they run slightly small.

Ugg Adirondack III Boots felt good on the first wear with no break-in pain to speak of. The brand's signature sheepskin lining makes these shoes exceptionally cozy, and the cushioned insoles offer excellent support. With superior traction and waterproofness, they're ideal for snowy and icy conditions. Though the rubber soles are thick, they're flexible and not as heavy as many other snow boots.

After reading buyer reviews, we ordered a half-size up, and this turned out to be the right choice, as we found they run slightly small. These winter boots are on the pricier end, but we think they're worth the investment considering the high-quality materials, durability, exceptional warmth, and comfortable feel right out of the box.

The Details: Sizes 5 to 12 | Leather or waterproof suede, sheepskin

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (17)

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (18)

We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (19)

Our Ratings

  • Durability

    5/5

  • Value

    5/5

  • Fit

    5/5

Why We Love It

  • Just the thing for frigid conditions, these boots feature luxuriously cozy linings, waterproof uppers, and high-traction soles.

What to Consider

  • Each boot weighs three pounds, and they may be too tight for those with wide calves.

We also like this suede pair from Overland. Despite the 2.5-inch heels, these boots were surprisingly comfortable. Our feet didn't hurt after walking over a mile — in fact, they felt great, thanks to the ample cushioning and built-in arch support. The thick shearling and wool linings add insulation and a luxurious quality. These boots aren't the most breathable, but if you need cold-weather footwear that keeps your feet warm and toasty, you can't go wrong.

The rubber outsoles also provided good traction on wet and icy ground, and the waterproof suede exteriors showed no signs of damage after several jaunts in inclement weather. They fit true to size, though the shafts might be too tight for people with wider calves. Additionally, each boot is three pounds, so account for the weight if you're packing for a trip.

The Details: Sizes 5.5 to 11.5 | Waterproof suede, merino shearling, wool

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We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (24)

Our Ratings

  • Support

    4/5

  • Durability

    5/5

  • Value

    5/5

  • Fit

    5/5

Why We Love It

  • These are the ideal streetwear boots, with a laid-back yet practical aesthetic and comfort features throughout.

What to Consider

  • Half-sizes aren't available in this style, and the lowish height may leave your ankles exposed to the cold.

Looking for a more laid-back streetwear style? Doc Martens Combs have your name on them. These boots fit true to size (though they only come in whole sizes) and work with thick athletic socks or casual crew socks. They feature "WarmAir" insulation to help retain warmth, which is ideal for the cold season. With padded footbeds, flexible uppers, and bouncy soles, they kept our feet happy when walking around and standing for long periods. We didn't experience any discomfort, even on the first wear, and felt they provided adequate support. Although these boots don't make any waterproof claims, the exteriors did seem to repel water and keep moisture out, which is always a bonus.

The Details: Sizes 5 to 11 | Nylon, rubberized leather

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Why We Love It

  • These durable, waterproof boots boast comfy cushioning; arch support; waterproofness; and a rugged, utilitarian aesthetic.

What to Consider

  • They're pretty stiff at first but break in quickly, and the dense rubber soles are a bit heavy.

The Bogs Holly Boots also fared well in our tests. They fit true to size, and while the structured leather uppers were stiff at first, they softened substantially with continued wear. The footbeds provide cushioning and arch support, while the tractioned outsoles prevent slips on slick ground. The leather is supposed to be 100 percent waterproof, and sure enough, our feet stayed dry in rainy, wet conditions. While the dense rubber soles add some weight, they're not uncomfortably heavy. You can count on these boots to keep you comfy for long hours on your feet, whether you're working outdoors, sightseeing, or hiking. We also like the rugged lace-up design, which you can rock with jeans or activewear.

The Details: Sizes 6 to 11 | Leather

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (26)

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (27)

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (28)

  • We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (29)

Why We Love It

  • These sophisticated, timeless knee-high boots are not only comfy but also waterproof and notably durable.

What to Consider

  • The price is not low, and they could be hard to fit in a suitcase.

We wore this sophisticated knee-high pair on various occasions: while commuting to work, at the office, on the weekends, and when going out at night. They stood up to heavy rain, keeping our feet dry while preserving the waterproof leather exteriors. These boots didn't require any breaking in, but you can count on the leather to soften to the shape of your feet and calves over time. The brand recommends ordering a half-size down from what you normally wear, but we thought they fit true to size with plenty of toe room. Due to the height, these boots might be hard to fit in a suitcase, though you could get creative and stuff the shafts with socks or underwear. While the steep price may be hard to justify, the quality was apparent as soon as we opened the box. Plus, they're undeniably stylish yet timeless, so you'll likely wear them year after year.

The Details: Sizes 4.5 to 10.5 | Leather

Other Women's Boots We Liked

We’ve tested so many shoes that they couldn’t all secure a spot on our list, but here are a few more that might work for some people.

Sam Edelman Garret Platform Boot: We found these boots to be very comfortable and loved the thick, almost bouncy lug soles. However, they were a bit tight in the toe area and might not be ideal for those with wider feet. Also, the rubber treads began to fray after several wears, which was disappointing.

Eileen Fisher Purl Sock Bootie: These were among the most comfortable boots we tested, and they don't rub whatsoever. That said, the knitted uppers aren't practical for wet climates, and the steep price might be hard to justify.

Vionic Sienna Leather Ankle Boot: We liked the Western-inspired style of these ankle booties and appreciated the waterproof design. While they were comfortable in the heels, the front of our feet felt squished and ripe for blisters. They did break in after a couple of days, though.

Our Testing Process

The Travel + Leisure team tested 93 pairs of women's boots across multiple tests, including our most recent tests for waterproof boots and snow boots to wear in real-world settings. We assessed the fit with different types of socks and wore them on multiple occasions over an ongoing, six-month testing period, walking around both indoors and outside. We took note of the feel; how rigid or flexible the materials were; how long it took to break them in; and whether the boots rubbed, chafed, or caused blisters.

If the boots were marketed for weather-resistance, we also evaluated them to see if they successfully kept water out and prevented slipping on slick ground. Each pair was scored for comfort, support, fit, durability, quality, and overall value, and those with the highest average ratings across all categories are featured in this roundup. We also specifically looked for products that we rated highly for comfort since this is a roundup of the most comfortable boots for women.

Tips for Buying Women's Boots

Know what you plan to wear them for

When shopping around for boots, think about where you plan to wear them and what you'll be doing. Do you have a ski trip, snowy hike, cold-weather sightseeing, fancy dinner, or networking event coming up? Or do you just need something to get you through the winter? If you plan on hiking in them, you’re going to want something with good traction and support, and if you plan on wearing them in the cold weather, you’re going to want something with insulation. In any case, the style should fit the occasion whether that’s formal or casual, and keep your feet not only comfortable but also warm and dry.

Consider comfort and support

According to Dr. Ramani, the most comfortable women's boots will have a modest heel height (she recommends no higher than 1.5 inches), a toe box with plenty of wiggle room, and a shaft that's not too tight. "The calf width should be roomy enough that you can put your finger in between your skin and the boot to allow for good circulation," she says.

If you plan to be walking around or standing for long periods, look for a pair with built-in arch support and cushioning as well — especially important when you're looking for the most comfortable heels to wear with a dressier outfit.

Select a versatile style and color

When you invest in a high-quality pair of boots, they should ideally hold up for multiple years. With this in mind, your best bet is to choose a versatile style and color rather than something that's simply on-trend for the current season. Consider a simple silhouette that goes with various outfits in a neutral hue, like black, brown, or camel. Plus, if you look for versatility, you’ll be more likely to get more use out of your boots both on your travels and at home, too.

Frequently Asked Questions

  • How long does it take to break in women's boots?

    Many of the boots we tried were comfortable right off the bat. However, leather styles can take some time to break in. If you wear them for a few hours a day, you can expect them to conform to the shape of your feet within a couple of weeks and get even more flexible over time. We recommend wearing the boots a few times before traveling in them because you don’t want them to get blisters on your next trip when you haven’t broken them in yet.

  • What type of boot is best for everyday wear?

    "If you're planning to wear a boot every day, look for a more rounded toe and a lower heel, like a Chelsea boot," says podiatrist Erin K. Koprince, DPM, DABPM. In addition to the modest heel, she says Chelsea boots usually have spacious, rounded toe boxes, not to mention a "chic look that never goes out of style." Ultimately, it comes down to personal style preferences.

  • How do you clean women's boots?

    The proper way to clean women's boots depends on the material. You can buff leather with a dry or damp cloth and polish it as needed with a leather-specific solution. If your boots are made of suede, use a cleaner specifically formulated for the material, and always do a patch test on a small area first to ensure it doesn't cause discoloration. Rubber boots can be wiped clean with a wet cloth or even rinsed off with water.

Why Trust Travel + Leisure

Theresa Holland is a commerce writer specializing in travel gear and apparel. For this story, she interviewed two podiatrists for tips on buying comfortable boots, then combed through insights from multiple tests done by the T+L team, and pored over product specs to craft thorough, well-researched recommendations. While researching women's boots, she spoke with podiatrist and foot surgeon Mona Ramani, DPM, and podiatrist Erin K. Koprince, DPM, DABPM.

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We Tested 93 Pairs of Shoes to Find the Most Comfortable Boots for Women (2024)
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