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. 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: Marc Fisher Ltd. Yale Chelsea Boots
  4. Most Comfortable Tall Boots: Naturalizer Axel 2 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: UGG Harrison Waterproof Moto Boots
  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: Vionic Bethany Ankle Boots
  14. Most Comfortable Slipper Boots: The North Face Thermoball Traction Booties
  15. Editor Favorite: Veldskoen Heritage Boots

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Madewell

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 three years ago for the first time, and again last 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 2021. In fact, this is the second pair she’s purchased in six 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 offers the same edgy vibe. These GBG combat boots have accumulated more than 500 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)

Nordstrom

3. Marc Fisher Ltd. Yale Chelsea Boot

Most Comfortable Leather Booties

Can boots be as comfy as a pair of sneakers? Turns out, yes, because these March Fisher Ltd. booties exist. There are nine beautiful colors to choose from and each pair can easily be dressed up or down to fit your personal style. Some reviewers suggest going a half size down for a snugger fit, but those with wider feet or anyone who likes to wear thicker socks (especially come winter) might prefer to stick with their true size. Multiple reviews mention how comfy these ankle booties are right out of the box with one saying she walked more than 2,000 steps in them without a single blister appearing. If you’re still not sold perhaps this rave review will do the trick: “I feel it is my civic duty to tell you this—These are the most comfortable shoes I have ever owned. They are like slippers you are allowed to wear in public. Very fashionable, socially-acceptable slippers. I bought these shoes on a whim but honestly my feet have never been so happy.”

Buy it ($179)

Verishop

4. Naturalizer Axel 2 Tall Boot

Most Comfortable Tall Boots

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 it. Oh, and did we mention both the boots themselves and the packaging are made from sustainable, eco-friendly materials?

Buy it ($240)

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 tons 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, its shoes are also surprisingly stylish. For this pair, you can choose from slick black or tan, and both 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 ($120)

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 at places like Nordstrom, Saks Fifth Avenue and Net-a-Porter.)

Buy it ($798)

Nordstrom

8. UGG Harrison Waterproof Moto Boot

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 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). An inner zipper makes it easy to slip them on and off. “It’s like wearing slippers all day,” confirms one PureWow staffer. “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.

Buy it ($160)

Zappos

9. Kamik Heidi Rain Boot

Most Comfortable Rain Boots

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. 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 857 reviews and a perfect five-star rating on Zappos, and a whopping 4,562 reviews on Amazon and 4.4 stars, we’d say these boots make for a pretty safe, and stylish, bet.

Buy it ($55)

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 for chic, weather-ready style year after year. The Jewel silhouette 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 need to be warm, have trustworthy 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 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 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!” Oh, and they also come in wide widths.

Buy it ($135)

Zappos

13. Vionic Bethany Boots

Most Comfortable Wide-Width Boots

Vionic is one of our favorite brands for wide-width shoes, but this classic Western design stands out from the pack for its timeless appeal and dedication to comfort. It comes in black and cognac brown, and the footbed was designed by podiatrists to provide all-day comfort and support at your heel, arch and the ball of your foot. They’re even waterproof, so you don’t have to worry if you run into a surprise rain storm. “I wore these boots walking the dog and playing in the park with him (about 2 miles altogether) the day I got them and they were great,” says one review. “I've worn them just about every day since I got them and I love them. I'm buying another pair in the black ASAP!”

Buy it ($160)

The North Face

14. The North Face Thermoball Traction Booties

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 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 to be found here), and both the sole and the insulated upper are made from eco-friendly, recycled materials. Speaking of that upper, the Lightweight ThermoBall Eco technology allows these super-lightweight slippers to keep your feet warm even when wet. They can also very easily be compressed to fit in a suitcase or backpack for comfort on the go. Reviews claim the Thermoball is a God-send 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.

Buy it ($65)

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 ($140)

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