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A fresh pair of fall boots is one of our favorite seasonal purchases to make. But we have to admit, sometimes the stylish block-heel croc booties we just couldn’t live without aren’t exactly ideal for walking or standing…let alone running after the bus on a regular basis. So rather than put our poor feet through the aches and pains of yet another cute but toe-pinching experience, we tracked down the most comfortable boots for any and all occasions—rain, sleet, snow, strolls through the park or even a night of dancing (you know, sometime late in 2021). Here are the ones that stood out from the pack and are well worth investing in.

Our winners at a glance:

  1. Most Comfortable Heeled Booties: Madewell The Regan Boots
  2. Most Comfortable Combat Boots: GBG Los Angeles Gessy Combat Boots
  3. Most Comfortable Leather Booties: Everlane The Day Boots
  4. Most Comfortable Tall Boots: Loeffler Randall Gia Tall Boots
  5. Most Comfortable Chelsea Boots: Blundstone Footwear Chelsea Boots
  6. Most Comfortable Wedges: Dr. Scholl’s Mania Wedge Booties
  7. Most Comfortable Over-the-Knee Boots: Stuart Weitzman The Lowland Boots
  8. Most Comfortable Cold-Weather Booties: Lucky Brand Baselsher Leather Ankle Booties
  9. Most Comfortable Rain Boots: Kamik Heidi Rain Boots
  10. Most Comfortable Water-Resistant Boots: La Canadienne Jewel Boots
  11. Most Comfortable Snow Boots: Sorel Winter Carnival Boots
  12. Most Comfortable Hiking Boots: Merrell Moab 2 Mid Waterproof Boots
  13. Most Comfortable Wide-Width Boots: LifeStride Adriana Booties
  14. Most Comfortable Slipper Boots: Teva Ember Mid Booties
  15. Editor Favorite: Veldskoen Heritage Boots

RELATED: 3 Podiatrist-Approved House Shoes (and 2 That Will Wreak Havoc on Your Feet)

Zappos

1. Madewell The Regan Boot

Most Comfortable Heeled Booties

Yes, it is possible to wear heels all day without soaking your swollen feet in an ice bath around 8 PM. Case in point: These 2 ½-inch block-heel booties from Madewell, which have gone through a few different iterations, but remain a steadfast favorite among all who buy them. The stretchy fabric panels make these boots easy to pull on and off, while the leather front and back of the shaft provide ample ankle support (a major key when it comes to finding comfortable heels). They come in both cognac brown and classic black, and while some reviewers found the toe box to be a little tight, Madewell suggests that the leather will slightly stretch and mold to the shape of your foot as you wear them in. “I bought these boots two years ago for the first time, and again this Thanksgiving,” says one repeat buyer. “I've gotten so many compliments on the pair, even after years of wear.”

Buy it ($178)

DSW

2. GBG Los Angeles Gessy Combat Boots

Most Comfortable Combat Boots

One PureWow editor loves these boots so much, she wore them four times a week last fall and winter and will likely do the same again in 2020. In fact, this is the second pair she’s purchased in five years. “I love that I can just zip them up and go,” she tells us. Indeed, the zipper and buckle combination is much more efficient than sitting down to lace-up a pair of traditional Dr. Martens but with the same edgy vibe. These GBG combat boots have accumulated more than 400 reviews on DSW and a 4.6-star rating, with nearly every customer rating comfort at a three out of four. They also have excellent traction for strolling along leaf-covered sidewalks after a cool autumn rain.

Buy it ($60)

Everlane

3. Everlane The Day Boot

Most Comfortable Leather Booties

Can boots be as comfy as a pair of sneakers? Turns out, yes, because these Everlane booties exist. There are six beautiful colors to choose from—black, espresso, cognac, gold metallic, stark white and ecru (pictured fabove)—and each pair can easily be dressed up or down to fit your personal style. Even those who regularly put their feet through the ringer (nurses, those who work on film sets and hairdressers) will find these chic ankle boots do good for their worn-out feet. Says one reviewer, “I’m a distance runner with unforgiving high arches. It is incredibly difficult to find a beautiful boot that I can wear daily. I have the Day Boot in several colors and they are well-worth the investment!” As for sizing, Everlane suggests that sizes 5 through 6.5 might run a little large, size 7 through 8.5 should fit true to size, and sizes 9 through 11 run a little small, so take that into consideration before you add to cart.

Buy it ($198)

Loeffler Ranfall

4. Loeffler Randall Gia Tall Boot

Most Comfortable Tall Boots

This stunning pair of classic tall boots from Loeffler Randall may be expensive, but will last for years and will only get more comfortable as they boots age. The interior includes a padded footbed, which counteracts any extra pressure from the 2-inch heel (FYI, podiatrists recommend a slight heel for winter boots to prevent your feet from over pronating). And while we’re particularly obsessed with this gorgeous deep espresso hue, they also come in black and cognac (a lighter, more reddish brown). “These are the boots you imagine chic Swedish women wearing,” one fan observes. “Great lines, perfect heel height, a cool shape you rarely see and beautiful in color. They fit well around my calves—both with jeans tucked in and on bare legs—without bunching or gaping. And I took my true size which feels comfortable out of the box.”

Buy it ($695)

Zappos

5. Blundstone Footwear Chelsea Boot

Most Comfortable Chelsea Boots

These rugged Chelsea boots come with an anatomically designed, shock-absorbing PORON XRD footbed—which basically just means these easy to pull-on booties are more than prepared for a full day of walking, standing and exploring. Front and back tabs make it easy to get them 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. I live in the country and spend a lot of time chasing my young kids through all kinds of terrain and these have stood up to mud and tree climbing and even fully submerged in a creek at one point.” Water- and child-proof? What more could a woman ask for?

Buy it ($200)

Dr. Scholl's

6. Dr. Scholl’s Mania Wedge Bootie

Most Comfortable Wedges

It should come as no surprise to find Dr. Scholl’s on this list. In addition to a slew of products designed to treat an array of foot ailments—sore insoles, ingrown toe nails, blisters, etc.—the brand also makes some of the most comfortable and supportive footwear around. Often, their shoes are surprisingly stylish. For this pair, you can choose from slick black, tan and gray with a natural wood heel, but all three options come with an impressive technologically advanced insole for extra cushioning and support at exactly the right pressure points. One shopper elaborates: “This boot…fits close to the ankle but has elastic so it stretches when you walk. The toe is almond shaped but has plenty of room for my toes. The wedge isn't too tall, so I can wear these all day without my feet hurting. Love love!” These booties are also made with eco-conscious and responsibly-sourced fabrics and with each purchase Dr. Scholl’s will donate one tree to Trees for the Future to help offset its carbon emissions.

Buy it ($125)

Stuart Weitzman

7. Stuart Weitzman The Lowland Boot

Most Comfortable Over-the-Knee Boots

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 most popular color is definitely black suede, but they’re also available in a light tan and gray-tinged white. The tie at the top ensures 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! 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.” (Yes, the price tag may be incredibly high, but you can often find these fan-favorites on sale throughout the year places like Neiman Marcus, Bloomingdale’s and Zappos.)

Buy it ($798)

Amazon

8. Lucky Brand Baselsher Leather Ankle Booties

Most Comfortable Cold-Weather Booties

If you’re not planning to trudge through the snow but still want to protect your feet from winter’s chill, try this faux shearling-lined bootie from Lucky Brand. “It’s like wearing slippers all day,” confirms one PureWow staffer. “Plus, a wider toe box means no pinched toes, even with chunky socks.” These chic ankle boots come in three colors—warm gray, matte black and cedar brown—all of which have been treated to be weatherproof. The slight heel, 1 ¼ inches to be exact, gives these a more stylish look than your typical fleece-lined boot, while the side zipper makes them incredibly easy to put on and take off. As another reviewer says, “I bought these for a recent trip to NY. I walked around the city in them for 3 days with no complaints. They were extremely comfortable and kept my feet warm, plus they looked adorable. Very happy.” 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.

$139 at Amazon

Zappos

9. Kamik Heidi Rain Boot

Most Comfortable Rain Boots

Galoshes may be a wonderfully practical option on rainy days, but they’re rarely all that 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. Oh, and did we mention that every element of the boot is 100 percent recyclable? 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 839 reviews and a perfect five-star rating on Zappos, and a whopping 3,667 reviews on Amazon and 4.4 stars, we’d say these boots make for a pretty safe, and stylish, bet.

Buy it ($50)

Zappos

10. La Canadienne Jewel Boot

Most Comfortable Water-Resistant Boots

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. All of the brand’s leather and suede boots are guaranteed waterproof for six months from purchase date, but can be treated again and again for chic, weather-ready style year after year. The Jewel style in particular has gained a lot of praise for its super stylish design coupled with complete ease of wear. A 2 ¼-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.

Buy it ($498)

Zappos

11. Sorel Winter Carnival Boots

Most Comfortable Snow Boots

A good pair of snow boots needs to be warm, have trustworthy traction and be flexible enough for walking through slush and ice, without flopping all over the place. And this Sorel pair checks all those boxes. The entire boot is waterproof and seam-sealed with a cozy faux-shearling cuff and felt liner that will protect your toes from Jack Frost. The lace-up front also allows you to control the amount 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 for me, 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 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.

Buy it ($150)

Merrell

12. Merrell Moab 2 Mid Waterproof Boots

Most Comfortable Hiking Boots

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 tired your feet feel, especially if you’re on a multi-day trek. This waterproof pair by Merrell has 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 got the same size as my running shoes. 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!”

Buy it ($135)

LifeStride

13. LifeStride Adriana Bootie

Most Comfortable Wide-Width Boots

LifeStride is one of our favorite brands for wide-width shoes, but this buckled ankle design stands out from the pack for its timeless appeal and dedication to comfort. It comes in black and dark brown leather as well as black and beige suede, and the footbed is made using LifeStride’s Soft System technology to provide all-day comfort and support at your heel, arch and the ball of your foot. It even has built-in shock absorption to keep that comfort going even through long days of museum tours or city exploration.

Buy it ($70)

Zappos

14. Teva Ember Mid

Most Comfortable Slipper Boot

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 Teva booties will keep your feet cozy, warm and comfortable. We love that they don’t look like your typical slipper (no suede or shearling to be found here), so you won’t get any sideways glances if you do end up wearing them to walk your dog around the neighborhood (no judgements here). They also offer a bit more foot support than most house shoes, meaning you’re less likely to develop pain as you might from a totally flat shoe. Per one enthusiastic reviewer, “I started wearing these a few weeks ago when the weather started to cool off a little and now I only want to wear these shoes. I've worn them to walk my dog, to run errands and also to hang out around a campsite. I got some oil splatter on them from camp cooking and they didn't stain at all! They are also VERY warm. When I put them on in September, my feet immediately started sweating. They take some breaking in around the ankles and I have to use the pull tabs to stretch the goring to get them on. But they are truly my new favorite shoes. Maybe I'll move to a cold climate so I can wear them year-round.”

Buy it ($90)

Veldksoen

15. Veldskoen Hertiage Boots

Editor Favorite

These suede booties are handcrafted in South Africa from locally, ethically sourced materials and are so comfortable you don’t even need to wear socks. The double-sided suede upper has an incredibly soft hand-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. And while they aren’t technically a wide-width shoe, lots of reviews mention the benefits of the wide 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 with the pieces in your wardrobe.

Buy it ($136)

RELATED: The 10 Most Comfortable Ankle Boots According to Foot Experts (AKA Podiatrists)

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