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1. Steve Madden ankle boots reviewers confirm are comfortable right out of the box, which means you can put them on as soon as they arrive at your door and then head out with a spring in your step because you've got a cool new pair of shoes.
FYI, if you have Amazon Prime you can try before you buy!
Promising review: "Can I just say Steve Madden nailed this one!!! I ordered two more pairs. These are so comfortable and stylish!!! I wear them all day and still comfortable! Perfect." —Cynthia
Get them from Amazon for $51.50+ (available in sizes 5.5–13, including wide sizes, and 14 colors).
2. Ugg ankle boots TikTok has caused to sell out several times, so I wouldn't be surprised if it happened again. The shorter version of your fave shoes growing up are now an easy and chic way to keep your feet warm all fall and winter long.
FYI, if you have Amazon Prime you can try before you buy!
Promising review: "Love, love, love these. So worth the price! So comfortable. I wore them all day and my feet were so warm and happy. They are adorable but look a bit like slippers. I loved them so much I ordered another pair today. I highly recommend them but only if you like your feet to be warm and cozy!" —Amy Del Santo
Get them from Amazon for $149.95+ (available in sizes 5–12 and in 29 colors).
3. Some over-the-knee boots for when you want to ~elevate~ your look but don't want to hinder your ability to walk all night long. Reviewers say these are super comfortable and worth it because the quality is made to last for years.
Promising review: "I was questionable at first as to if I would like these or if they would be good quality, but boy was I proven wrong about questioning. They are now my favorite boots. I wear them all the time for work, to events, to going out, etc. They work for everything, and I can walk in them for hours, and I hate wearing heels for extended periods. They are cute, go with everything, can be worn anywhere, and are easy to clean if they ever get messy. The perfect boot, and I’ve worn them for a couple of years now still walking as good as the day I received them." —Jacklyn
Get them from Amazon for $28.79+ (available in sizes 5–11 and four colors; more colors here).
4. Doc Marten lace-up boots so reliable, you can wear them through rain, sleet, and even snow without compromising your style.
FYI, if you have Amazon Prime you can try before you buy!
Promising review: "I love these boots. I did have to go up in size because there weren't half sizes. I love them. They're so comfortable. I can wear them all day. I stand doing hair all day and have no fatigue at all. Can’t say enough channeling my inner '90s high schooler. Tons of compliments. Very happy with the purchase. They are so soft and the second wear they are broken in!" —Amazon Customer
Get them from Amazon for $151.70+ (available in sizes 5–11 and in seven colors).
5. Glove boots basically screaming to be worn on those crisp fall mornings when you step outside and take a big breath, feeling all the possibilities that the season brings. There's nothing stopping you when you have these babies on your feet.
Promising review: "This boot fits like a glove and hugs your feet giving your ankles support throughout the day. I wore these boots on day one and two for 12 hours each day. I work retail so I'm on my feet ALL day on tile flooring which can be extremely painful at times but these boots are awesome!! I will be ordering another pair." —TazN
Get them from Everlane for $105 (originally $150; available in sizes 5–11 and in three colors).
6. A pair of chunky ankle boots more than 9,800 reviewers recommend because they're comfortable, easy to walk in, and, oh, look badass, too. Get ready to ~strut~ when you wear these.
Promising review: “These booties are perfect to wear with just about anything! They are very comfortable even if you're on your feet all day. As a teacher, it is important to have comfy shoes, but I want them to be stylish as well. These shoes definitely do both! They fit true to size.” —Janet
Get them from Amazon for $38.98+ (available in sizes 5.5–11, wide and in 10 colors).
7. A pair of cowboy boots you can ~boot scootin' boogie~ in all across town and feel like a star. They'll be with you for concerts, vacations, or just nights out with your friends.
Matisse Footwear is a Los Angeles-based small business creating affordable and fashionable footwear.
Promising review: "I ordered these boots and wore them for the first time for 12 hours straight in Nashville, Tennessee. I walked all day in them and danced all night in them. They were extremely comfortable!! My feet did not hurt in them at all. I even wore them the next day for another nine hours, and my feet felt great! These boots are true to size. Great purchase!!" —Alyson
Get it from Amazon for $51.50+ (available in sizes 6–11, wide widths, and in 19 colors).
8. A pair of chunky mid-calf boots you can either get in a neutral solid color or with a brightly-colored sole, depending on your vibe. Either way, you'll have a great pair of shoes that reviewers confirm are easy to walk in, even with the slight platform.
9. Square-toe ankle boots actually designed to be waterproof so you can wear them all day knowing that the random mid-afternoon fall rainstorm isn't going to stop you in your tracks. You can continue on like the boss you are.
Promising review: "I just purchased the ankle boots, and I wore them for a day at work. I am on my feet all the time. I felt like I was bare-footed in these! Unbelievably comfortable. I will soon purchase another pair in a different color. I'm so happy to have found these!" —Anne J.
Get them from Vivaia for $149 (available in sizes 5–11 and in six colors and patterns).
10. Faux-fur trim waterproof boots that are basically the shoe equivalent of having beauty and brains because not only are they super cute, but they're also temperature-rated up to -11 degrees F. This means they'll ~stand~ up to all those epic winter adventures you have planned.
Promising review: "After trying on tens of other brands of boots, I can tell you that these ones are PERFECT! They are SUPER comfortable! I walked an average of 13k steps per day for 20 days on them for my Europe winter trip and my feet and back never hurt! They are warm enough for a 25-degree weather with the right socks. I haven't had the chance to try them in rain yet, but they are supposed to be water-resistant. They are true to size, and there's even enough room to wear thick or double socks without feeling too tight. And the best part, they are beautiful and fashionable." —Nordstrom Customer
Get them from Nordstrom (available in sizes 6–11 and in nine colors) or Cougar Shoes (available in sizes 6–11 and in 12 colors) for $170.
11. Trendy pointed-toe knee-high boots with a block heel that makes them easy to walk in. With these in your closet, you'll be able to transition all your favorite dresses into fall and winter.
12. A pair of Sorel Chelsea boots made to be fully waterproof. Gone are the days when you have to wear really ugly shoes when it's raining because you don't want to ruin your favorite cute pair. These boots can (and will) be both for you.
FYI, if you have Amazon Prime you can try before you buy!
I got these boots last fall and wore them around New York for four days straight. I walked so much and my feet were comfortable the whole time. I highly recommend!
Promising review: "Love all of my Sorel boots/shoes! They are very comfortable!! And super cute! I get a ton of compliments! And I’m a cosmetologist, so I’m on my feet all day!" —Stace
Get them from Amazon or Sorel for $142+ (available in sizes 5–12 and in four colors).
13. A glamorous Chelsea boot I'm *pretty* sure Hannah Montana was referencing when she sang, "You get the best of both worlds" because they combine style and comfort into one great shoe you'll wear ALLL the time.
Promising review: "Love these boots. They slip on and off easily. They are so comfortable. I do a lot of walking/standing and I am able to wear them all day. Can easily dress them up or down. Will definitely buy again and in white. NOTE: They do scratch easily but I'd still buy again." —Amazon Customer
Get them from Amazon for $39.99+ (available in sizes 6–11, including wide sizes, and in white and black).
14. Lace-up hiking boots you don't have to be an outdoorsy person to wear — these are great for those cold but not snowy days when you need to keep your feet warm and comfortable. Reviewers say these are even great traveling shoes!
Promising review: "LOVE. I’m an 8, wider food typically. These are so comfortable to wear for hours. I just traveled in them through the airport and wore them basically all day. I also wore them in the snow for a bit. Comfortable and nice! Cozy but not bulky. Definitely recommend." —Azmama
Get them from Target for $44.99 (available in sizes 5–12).
15. Free People slouchy boots many reviewers love so much that they return years later to buy another color — meaning you'll have more opportunities to wear these stellar boots with all your favorite outfits.
Promising reviews: "Top rated for a reason!! I love these boots and had a pair for 3 years, and eventually added other colors due to how much I love them" —kellyannkiernan
"I vacillated about the color of this boot when purchasing. I finally decided on the 'natural cane.' I couldn’t be happier. They are not only extremely comfortable but absolutely adorable. I am a teacher, and I can stand in these all day. If you have the opportunity, BUY THEM!!!" —DayZee72
Get them from Free People for $198 (available in sizes 6–11 and nine colors).
16. A pair of faux-suede heeled chelsea boots, which may look like a lot, especially if you don't like heels, but reviewers say these are super comfortable even if they're out of your ~comfort~ zone. You'll be able to walk around all day and you feet will feel the same as they do when you wear flats.
Promising review: "I really like these shoes a lot — they're incredibly comfortable for being heeled boots and I can stand in them all day at work. While I've only gone through one winter with these so far (in Chicago), they still look great! I also sprayed them with water protectant and it didn't affect the suede material at all, so I would 10/10 recommend these." —Sarasri
Get them from Amazon for $30.81 (available in sizes 5–11 and in seven colors).
17. Kenneth Cole boots you can count on as a wardrobe staple for years to come because these shoes aren't going anywhere. They have an elastic ankle panel that makes them easy to get on and off and just a slight heel, which means you can wear them for both casual and nicer occasions.
FYI, if you have Amazon Prime you can try before you buy!
Promising review: "These are the most comfortable boots I’ve ever worn! I have wide feet. I live in Florida and hardly wear more than flip-flops and sandals. I needed something for the colder weather and a trip to New England in February. I walked all over Boston all day long and my feet felt amazing even with the small heel. Best choice I’ve ever made!" —melis4806
Get them from Amazon for $109+ (available in sizes 5–11 and in seven colors).
18. A pair of waterproof Columbia boots so you can actually go on all those nature hikes you've been talking about for years now. They'll keep your feet protected and comfy so you don't have a moment like Reese Witherspoon in the movie Wild where her feet are all beat up and she throws her boot off the mountain.
FYI, if you have Amazon Prime you can try before you buy!
Promising review: "Ordered these last minute for a hiking trip in CO. Spent all day in these for the first time at Pikes Peak. They were comfortable, warm, and had good traction for climbing. I have wide feet and a bunion, but I was able to order true to size and be comfortable in them." —Adrian
Get them from Amazon for $60+ (available in sizes 5–12, wide, and in 17 colors).
19. Western-style ankle boots with velvet and snakeskin accents for a statement-making look everyone will go ~wild~ over.
Promising review: "I love these boots. I have them in another color. I have an unusually narrow foot. As with all boots, I wear a thick sock and use an insert. I can wear these all day long with no discomfort. Perfect heel height." —Dev
Get them from Amazon for $59.95 available in sizes 5.5–11 and three colors).
20. Lace-up boots you'll have around for longer than you expect because they never go out of style. They'll be with you for all those fun adventures and outings you do with friends because you know you'll be able to wear them all day long.
FYI, if you have Amazon Prime you can try before you buy!
Promising review: "Love these boots. Very comfortable, though I did order a half-size up. I can wear them all day without any problems. Price was fantastic and would recommend to anyone thinking of buying." —Tuppny
Get them from Amazon for $33.50+ (available in sizes 5–13 and in four colors).
21. Chunky-heel booties you can confidently wear to work (even if you work on your feet) and look professional and put together. And I know day-to-night dressing isn't really a thing anymore, but, boy, will these look great when you go out, too.
Promising review: "Amazing shoes! So beautiful and COMFORTABLE. Wore them all day at work, and they didn’t bother me at all. I’m on my feet most of the day at work, and there’s no way I could wear any other heel at work. Do size up though!" —Alana
Get them from Amazon for $41.99+ (available in sizes 5.5–11 and 12 colors).
The reviews for this post have been edited for length and clarity.