15 of the Most Comfortable Boots That Won’t Leave You With Blisters After Just One Wear

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The most comfortable boots for women are those you can wear right out of the box and for days on end. And while we must admit we’re kind of a sucker for trendy sky-high platform booties, they aren’t exactly ideal for walking...or even standing, for that matter. Rather than put our poor feet through the aches and pains of yet another cute-but-toe-pinching experience, we’ve made up our minds to track down the most comfortable boots for any and all occasions, from strolls through the park to a night of dancing, come rain, sleet or snow. Here are 15 styles that stand out from the pack and are well worth investing in.

The Most Comfortable Boots at a Glance

The Best Chelsea Boots for Women, Starting at $53

Most Comfortable Lace-Up Boots

1. Madewell Leather The Rayna Boots


• Why We Love Them: Inner padding, slip-resistant

“I am so excited to wear these boots all year-round,” says Operations Director of Branded Content Rachel Gulmi. “I’ve been wearing them a ton since buying them, and they’re so comfy and needed no breaking in.” Indeed, these leather boots may look rigid, but they’re actually very supple. Plus, they come with Madewell’s proprietary MWL Cloudlift Lite padding in the sole for bonus cushion and comfort. Although they aren’t weather-resistant, the lug sole gives you plenty of traction for walking on wet sidewalks or snowy driveways. And for an eco-friendly boost, that very same sole is made from 30 percent recycled materials. They come in classic black, off-white, deep burgundy and saddle brown.

Size range: 5 to 12

Most Comfortable Boots for Wide Widths

2. Hush Puppies Amelia Chelsea Boots

Hush Puppies

• Why We Love Them: Waterresistant, PureWow Editor-in-Chief approved

“I’ve been wearing these basically every day since October 1,” says PureWow Editor-in-Chief Jillian Quint. She raves about how comfortable and durable they are straight out of the box, and like almost all Hush Puppies boots, they come in wide widths in sizes 6 through 11. This style is also available in both a classic, pull-on Chelsea boot and a lace-up style, both with the same lightweight lug sole and cushioned insole. And both have been treated for water-resistance, so you can wear them in all kinds of weather without stressing about ruining that beautiful suede.

Size range: 6 to 12, regular and wide

Editors’ Pick

3. Margaux Suede The Downtown Boots


• Why We Love Them: Padded insole, 5 neutral colorways

“As a fashion editor, I am always torn between wanting to wear the coolest, funkiest styles I can find and also not wanting to tear up my poor feet,” says fashion editor Abby Hepworth. “But these boots are both incredibly chic and super comfortable, so I can run around the city in them without sacrificing style or comfort.” The sleek leather style comes with Margaux’s signature padded insole that works to combat any pressure put on your arches by the 2.5-inch stacked heel. As for sizing, this style is designed specifically to be worn with thinner socks, so if you’re hoping to wearing them with thick wool socks come winter, you might want to go up half a size. “I highly suggest double checking the size chart since these are sold in European sizes,” adds Hepworth. “I ended up going up a half size from my usual and I’m very glad I did.”

Size range: 3 to 13.5, narrow, medium and wide

Most Comfortable Cold-Weather Boots

4. UGG Suede Lakesider Heritage Boots


• Why We Love Them: Signature UGG plush lining, easy slip-on

If you’re not planning to trudge through the snow but still want to protect your feet from winter’s chill, try these wool-lined booties from UGG. They’re seam-sealed and waterproof to keep out moisture, and are every bit as comfortable and warm as the brand’s classic booties (which are not acceptable winter boots, by the way). A wide lace-up front makes it easy to slip them on and off. “It’s like wearing slippers all day,” confirms PureWow Director of Affiliate Strategy Pam Masin. “Plus, a wider toe box means no pinched toes, even with chunky socks.” While these booties might be ideal for exploring the city or commuting to work during the winter months, keep in mind they may not be warm enough for long outdoor excursions when temperatures are under 30 degrees.

Size range: 5 to 12

Most Comfortable Ankle Boots

5. Blondo Dahlia Booties


• Why We Love Them: Podiatrist-recommended, room for toe movement, color range

These boots actually come recommended by Dr. Miguel Cunha, a board-certified podiatric surgeon and founder of Gotham Footcare in NYC. He’s a fan of Blondo in general for the brand’s dedication to waterproof materials and generous toe boxes. The Dahlia style in particular has a wide toe box, is supportive, durable and slip-resistant, and features a 1.5-inch heel (it actually adds 2.25 inches to your height thanks to a .75-inch platform). Although we often think of waterproofing for rain, snow or winter boots, Dr. Cunha recommends seeking this feature out as often as possible to help prevent bacteria or fungi from growing in the shoe, or worse, on your feet. They come in cognac, chocolate, black and a sandy beige hue.

Size range: 5.5 to 10

Most Comfortable Chelsea Boots

6. Blundstone Leather Chelsea Boots


• Why We Love Them: Slip-resistant sole, minimalist styling

These rugged Chelsea boots come with an anatomically designed shock-absorbing extra XRD footbed, which basically just means they'll have you more than prepared for a full day of walking, standing and exploring. Front and back tabs make them easy to get on or off, plus the leather upper is water-resistant, making this Australian staple a stylish option for rainy days. “Right out of the box, these were almost perfect,” raves one shopper. “It only took two days to break them in, and now, two weeks in, they fit like gloves.” What more could a gal ask for?

Size range: 6 to 11

Most Comfortable Tall Boots

7. Naturalizer Leather Axel Boots


• Why We Love Them: Stretchy shaft accommodates calfs, wide widths available

This gorgeous pair of classic tall boots from Naturalizer has a trendy square-toe (but not too square, so it won’t feel out of style in a year) and has the added bonus of being totally waterproof. “I've owned Naturalizer boots in the past, and they held up well and were comfortable, so I decided to give these a go, too,” reads one review. “I wore them all day on my first try and no blisters or sore feet.” The heel is under 3 inches, but the footbed is also cushioned to counteract any pressure on the balls of your feet and keep your toes feeling happy all day long. (FYI, podiatrists recommend a slight heel for winter boots to prevent your feet from overpronating.) The back of the shaft is made from a stretchy fabric to better accommodate calves of different shapes and sizes, but these boots also come in wide widths for those who want that. Oh, and did we mention both the boots themselves and the packaging are made from sustainable, eco-friendly materials?

Size range: 4 to 12, regular and wide

Most Comfortable Over-the-Knee Boots

8. Stuart Weitzman Suede The Lowland Boots

Stuart Weitzman

• Why We Love Them: Leg-lengthening style, stretchy suede

There’s a reason so many supermodels, fashion editors and jet-setting celebrities have been spotted wearing these Stuart Weitzman boots—they’re the perfect combination of comfortable and chic. The tie at the top ensures there'll be no slipping throughout the day, while a slight stretch in the shaft allows these boots to easily conform to legs of all shapes and sizes. Plus, the soft leather insole molds to fit the exact contours of your foot over time. They also come in both narrow and wide widths. “These boots are GREAT!" wrote one enthusiastic reviewer. "I have a very high arch, and often cannot do pull-on boots that do not have a zipper, but this suede is so soft and flexible they pulled right on with comfort, yet still hugged the calf perfectly.”

Size range: 4 to 11

Most Comfortable Wedges

9. Aerosoles Brandi Ankle Boots


• Why We Love Them: Vegan leather, available in regular and wide widths

Wedges are a great way to add height without putting as much stress on your arches or the balls of your feet as a traditional heel. And this Aerosoles pair has the added bonus of a supremely supportive sole that’s been specifically designed to keep your feet feeling good on long walks or while standing for extended periods. The site suggests these do run a half-size large, so take that into account when ordering. They also come in wide widths in all seven color options if you’re in need of some extra toe room. Reviewer Monica P. writes, “Love these! Great fit, comfortable, love the look. I can’t do heels any more thanks to arthritis, but these give me the right lift without the pain!”

Size range: 6 to 12, regular and wide

Most Comfortable Rain Boots

10. Kamik Heidi Boots


• Why We Love Them: Generous opening, removable footbed, 100 percent recycled

Galoshes may be a wonderfully practical option on rainy days, but they’re rarely comfortable for all-day wear. Not this Kamik pair, however. A cushioned footbed offers enough support to make trekking through a thunderstorm feel almost pleasant. (Plus, the footbed is removable, so you can always slot in your own insoles if needed.) The rubber is also incredibly lightweight, and the 11-inch shaft provides enough coverage to prevent water from seeping in without restricting leg movement, a common complaint with taller rain boots. Not to mention, every element of the boot is 100 percent recyclable, so if your pair has reached the point of no return, you can box them up and send them back to Kamik to be recycled. With more than 5,000 reviews at Amazon and a perfect 5-star rating on Zappos, we’d say these boots make for a pretty safe, stylish bet.

Size range: 6 to 11

Most Comfortable Snow Boots

11. Sorel Winter Carnival Boots


• Why We Love Them: Extra-grip traction, faux-shearling cuff

A good pair of snow boots need to be warm, have reliable traction and be flexible enough for walking through slush and ice without flopping all over the place. This Sorel pair checks all those boxes. The entire boot is waterproof and seam-sealed with a cozy faux-shearling cuff and a felt liner that will protect your toes from Jack Frost. The lace-up front also allows you to control the amount of ankle support you want and need and can be adjusted for a wider foot or calf. They even work well for those who suffer from plantar fasciitis, as per this review: “I have long skinny feet and plantar fasciitis, so it's extremely hard for me to find shoes that work, let alone a winter boot, but I think this is it! Plus, they are super stylish, which is a total bonus.” Some commenters recommend going a one-half size up to accommodate thick socks (although they are incredibly warm, even with a thinner pair), but otherwise, these winter boots should fit true to size.

Size range: 5 to 12

Most Comfortable Hiking Boots

12. Merrell Moab 2 Boots


• Why We Love Them: Protective toe cap, waterproof

When you’re out in the wilderness clambering over rocks and hiking up mountains, the last thing you want to be thinking about is how sore your feet feel, especially if you’re on a multi-day trek. These waterproof boots by Merrell have been nicknamed the “Mother of All Boots” in the hiking community for their short break-in period and superior comfort—not to mention their ability to keep feet dry while still feeling breathable. A contoured footbed with extra arch and heel support means your feet will stay happy, even if you’re up in the mountains for a week (or longer). One recent Moab convert writes, “These are amazing. I wore them around my apartment a few times to break them in, but they didn’t even need it. Fit was perfect. ... I did an 8-mile backpacking trail, half of which was a very wet riverbed, and these are truly waterproof! I was on rocky trails, steep inclines, and lots of wet clay, and I didn’t lose my footing once. Merrell for life!” Oh, and they also come in wide widths.

Size range: 5 to 11, regular and wide

Most Comfortable Water-Resistant Boots

13. La Canadienne Suede Joanie Boots

La Canadienne

• Why We Love Them: Comfy memory foam insole, stylish round toe

If you just can’t get on board with the look of traditional rain boots, you can always opt for a more fashion-forward pair that just happens to be waterproof. And few companies nail this concept better than La Canadienne. It has tons of chic leather and suede boots that are guaranteed waterproof for six months from purchase date, but can be treated for weather-resistance year after year. The Joanie silhouette in particular has gained a lot of praise for its super stylish design coupled with complete ease of wear. A 2.5-inch heel gives you just enough lift, while the soft shaft provides ankle support that isn’t too stiff. As one shopper notes, “Well worth the investment. I don't usually like wearing heels, but these are extremely comfortable and sturdy. Bottom line, they’re very comfortable, extremely stylish, waterproof and warm.” A quadruple threat, if ever there was one.

Size range: 5 to 11

Most Comfortable Slipper Boots

14. The North Face Thermoball Traction Boots

The North Face

• Why We Love Them: Washable insole, eco-friendly

Whether you’re looking for something to wear around your campsite or just to pick up the newspaper from the end of the driveway, these The North Face booties will keep your feet cozy, warm and comfortable. We love that they don’t look like your typical slipper (no suede or shearling here), and both the sole and the insulated upper are made from eco-friendly, recycled materials. Speaking of that upper, the brand's proprietary ThermoBall technology allows these super-lightweight slippers to keep your feet warm even when wet. In fact, reviews claim the ThermoBall is a godsend for those with perpetually cold toes. “I get super cold feet and wanted good traction. These slippers fit the bill perfectly. What I particularly like is the insole can be removed and washed separately,” reads one review. And they also extol the benefits of the high-traction sole, which makes these a comfy option for walking the dog mid-winter as well as cozying up indoors. Better yet, they can also very easily be compressed to fit in a suitcase or backpack for comfort on-the-go.

Size range: 5 to 11

Most Comfortable Chukka Boots

15. Veldskoen Suede Hertiage Boots


• Why We Love Them: Lots of toe room, handcrafted by African artisans

These suede booties are handcrafted in South Africa from locally, ethically sourced materials and are reportedly so comfortable that you won’t even need to wear socks. The double-sided suede upper has an incredibly soft feel that conforms and molds to your feet after just a few wears and continues to become even comfier the more you wear them. The material is naturally weather and rain-resistant, so you don’t have to worry about being precious with them, either. And while they aren’t technically a wide-width shoe, lots of reviews mention the benefits of the larger toe box, especially for anyone with bunions or those who struggle to find shoes that don’t squish their toes.

“I’ve had my boots for a couple of weeks now, but the real test was four days of walking around Fredericksburg,” reads one review. “Absolutely LOVE these boots! They were comfortable when I put them on but have become even more so after wear.” Of course, we can’t forget to mention that wonderful pop of pink on the sole and laces. In fact, there are eight colors to choose from (including classic black and a muted gray), so you can have fun mixing and matching them with different looks.

Size range: 5 to 12

Why You Should Trust Us

PureWow is the best friend you never had when it comes to finding the best, most useful lifestyle products online. Founded in 2010, our company’s editors and writers have spent more than a decade shopping online, digging through sales and putting our home goods, beauty finds, wellness picks and more through the wringer—all to help you determine which ones are actually worth your hard-earned cash. From our PureWow100 series, which sees each and every item we test being ranked on a 100-point scale of awesomeness, to the painstakingly curated lists our fashion, beauty, cooking, home and family editors create as vertical experts, you can trust that our recommendations include some of the greatest items you’ll find on the internet. Whether you're looking for travel-size hair dryers you can take on-the-go or women’s walking shoes that won’t hurt your feet, we’ve got you covered.

Abby Hepworth is a PureWow editor obsessed with all things fashion and running related. Need recs on new training sneakers or GPS watches? She's got you covered. Want to stock up on all the trendiest clothes on a budget? She's here for you.

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