Unless specified otherwise, all sizes mentioned here are in women's sizing.
1. Steve Madden ankle boots are praised by reviewers for being comfortable right from the start, which means you can wear them as soon as they arrive and immediately enjoy the comfort and style they offer for your daily outings.


2. A pair of timeless Uggs to keep your feet cozy, warm, and as soft as a lamb’s fleece!

3. Ugg ankle boots have been a TikTok sensation, selling out multiple times. It wouldn’t surprise me if they fly off the shelves again. The shorter version of the classic shoes you loved as a kid now offers an easy and chic way to keep your feet toasty throughout fall and winter.


4. A pair of ultra-flexible over-the-knee boots that pair perfectly with any mini dress or skirt to keep your legs warm. With two-inch block heels, you can enjoy a leisurely walk without worrying about sore feet.


5. Doc Marten lace-up boots are so dependable, you can wear them through rain, sleet, and even snow without sacrificing your style.

6. Glove boots are practically calling out to be worn on crisp fall mornings when you step outside, inhale the fresh air, and embrace the possibilities of the season. When you have these on your feet, nothing can hold you back.


Promising review: "These boots fit like a glove, providing excellent ankle support all day long. I wore them for 12 hours each on the first two days. As someone who works in retail and spends all day on tile floors, my feet can get sore, but these boots are incredible! I’ll definitely be ordering another pair." —TazN
Available from Everlane for $150 (sizes 5–11, four color options).
7. A pair of chunky ankle boots that over 9,800 reviewers recommend for their comfort, ease of walking, and bold, badass style. Get ready to strut your stuff when you slip these on.


8. A pair of cowboy boots that are perfect for your ~boot scootin' boogie~ across town, making you feel like a star. Whether you're heading to concerts, going on vacation, or just out with friends, these boots will be your trusty companion.

9. A pair of Franco Sarto mid-calf boots that practically demand to join you on every adventure this year. Wearing them means you're not just walking—you’re S-T-R-U-T-T-I-N-G down the street.

10. A pair of chunky mid-calf boots available in a classic neutral or with a bold, brightly-colored sole, depending on the mood you're going for. Either way, you'll be stepping out in style with shoes that reviewers say are comfortable to walk in, even with the slight platform.


11. Square-toe zip-up ankle boots designed to be waterproof, so you can wear them all day without worrying about the random afternoon rainstorm. Keep walking with confidence, knowing the weather won’t slow you down.


12. Faux-fur trim waterproof boots that are the perfect mix of style and practicality. Not only do they look super cute, but they're also temperature-rated to withstand up to -11 degrees F. These boots will be your reliable companion for all your epic winter adventures to come.


Get them on Amazon for $149.99+ (originally $170; available in sizes 6–11 and nine colors).
13. A pair of Sorel Chelsea boots designed to be completely waterproof. Say goodbye to the days of choosing between ugly shoes and ruining your favorite cute pair when it rains. These boots give you the best of both worlds.


Just a heads up, if you have Amazon Prime you can try them on before committing to buy!
I bought these boots last fall and wore them around New York City for four days straight. I did a lot of walking, and my feet stayed comfortable the entire time. I highly recommend them!
Promising review: "I love all my Sorel boots/shoes! They are incredibly comfortable!! Plus, they're super cute! I get tons of compliments! And I'm a cosmetologist, so I'm on my feet all day!" —Stace
Available on Amazon for $54.56+ (sizes 5–12 and in six colors).
14. A chic Chelsea boot that I'm *pretty* sure was the inspiration behind Hannah Montana's song, "You get the best of both worlds," because it flawlessly blends style and comfort into a single pair of shoes that you'll be wearing ALL the time.


15. Sam Edelman ankle boots featuring padded insoles and a 2.25-inch platform, perfect for adding a bit of extra height without the discomfort of heels. These boots are vacation-ready and comfortable enough for a full day of city sightseeing without blisters or fatigue, as one reviewer confirms.


16. A pair of faux-suede heeled chelsea boots, which may seem intimidating if you're not a fan of heels, but according to reviewers, these are incredibly comfortable even if they push you out of your ~comfort~ zone. You'll be able to stroll all day with your feet feeling just as comfortable as when you're wearing flats.


17. Kenneth Cole boots that are destined to remain a key part of your wardrobe for many years. With an elastic ankle panel for easy on and off and a subtle heel, these boots are versatile enough for both laid-back days and more polished events.


18. These waterproof Columbia boots are your ticket to finally conquering those long-awaited nature hikes. With these boots, your feet will stay comfy and protected, so you won’t experience a moment like Reese Witherspoon in Wild, where she struggles with her battered feet and throws her boot off the mountain.


19. Western-inspired ankle boots featuring velvet and snakeskin details for a bold, eye-catching look that’s sure to turn heads wherever you go.

20. Classic lace-up boots that will stick with you for years to come, as they’re timelessly stylish and perfect for all your exciting adventures with friends. You can count on them to be comfortable for all-day wear.

Chunky-heeled booties that are perfect for professional settings, even if you're on your feet all day. They're also great for evening outings, blending work and play effortlessly.


22. For those days when you want to look effortlessly cool and feel comfortable, Dr. Martens Chelsea boots are your perfect match. These boots are bound to become your go-to pair for any season, offering timeless style and lasting comfort.

23. Square-toe boots are a versatile addition to your closet, effortlessly combining comfort with class. Whether you're pairing them with casual jeans and a T-shirt or dressing them up with a chic skirt and blouse, these boots give you the flexibility to define your own style!


24. Columbia hiking boots that are waterproof, allowing you to combine style with practicality whether you're hiking up a mountain or just strolling around. These boots are designed to handle it all—fashion and function, no problem.

25. These platform heels are perfect for giving any outfit a major upgrade. With a bold 5.3-inch heel and a cushioned insole, they offer extra height without the discomfort you'd expect from traditional heels.

Koi Footwear is a UK-based small business that creates 100% vegan shoes!
You can grab a pair from Koi Footwear for $90 (available in US sizes 3–8).
26. These reliable lace-up boots feature a cozy faux-fur lining and anti-slip soles, perfect for navigating through rough weather. And the best part? You won't have to endure the dreaded break-in period that usually leaves your heels sore and blistered.


27. These quilted rain boots will ensure gloomy weather never spoils your day. Standing apart from typical rain boots, they boast a chic quilted design that reaches mid-calf for extra style and protection.


28. Waterproof Timberlands are a go-to in the boot world for a good reason. These boots are not only incredibly comfortable but also classic and built to last. Once you add them to your collection, you'll wonder how you ever lived without them.

29. A stunning pair of suede booties featuring a distinctive round heel and a pointed-toe design that won’t have you wincing in discomfort. These boots are designed to zip on and off effortlessly, making getting ready or unwinding a piece of cake.


Ma'am is a woman-owned small business based in LA that focuses on creating stylish, everyday shoes while prioritizing sustainability and comfort.
Customer Review: "New shoes can often feel uncomfortable on the first day, especially with long hours on my feet. I’m happy to share that these were an absolute delight to wear – it felt like I’d had them for months, they were that comfy! I sized up by half a size and I'm so glad I did. Proud to join the Ma'am club, and I’ll definitely buy more soon!" —Ashley Cornett
Get them from Ma'am for $300 (was $350; available in sizes 5–11).
30. Sam Edelman combat boots are the ultimate confidence boosters. Slip into these and you’ll feel like a total boss, all while keeping your feet comfortable for hours on end.

31. Blundstone Chelsea boots are the perfect pick if you've been eyeing them for a while and are waiting for a sign to finally make the purchase. They're water-resistant, provide excellent grip, and come with a removable comfort footbed — making them as cozy as they are stylish.

32. Peep-toe booties offer a playful twist on the classic shoe, letting you show off your polished toes. And if you're concerned about comfort, don’t be! The adjustable Velcro ankle strap ensures a snug fit with no slipping, providing all-day ease.


33. Sparkly ankle boots to add a bit of excitement to your wardrobe when you're tired of the usual footwear. If you crave a little sparkle without sacrificing comfort, these boots are made for you.


34. A pair of faux leather quilted knee-high boots that might make you look like a professional horseback rider at least once. They’re stylish, comfy, budget-friendly, and come with so many adorable details that you'll be showered with compliments wherever you go.


35. A kitten heel boot that pairs perfectly with everything from skirts and dresses to jeans, making it a wardrobe staple. If you're always on the move and need to stay on your feet all day, these boots will keep you comfy throughout your busy schedule.


Promising review: "I work in retail at a massive 12,000 sq ft store. I can wear these boots for my entire 9-hour shift, running around the store, and still feel great afterward. The first time I wore them, I had a little discomfort, but since then, they've been incredibly comfortable. Consider this your sign to buy these shoes." —Isabella
Get them from Dolce Vita for $159.90+ (originally $250; available in sizes 5–13 and in three different colors).
36. Western boots are, in my opinion, better than a roundtrip flight to Nashville (no long security lines, no baggage fees, etc.). These knee-highs feature a comfy, chunky heel, soft jersey lining, an anti-slip sole, and pull tabs, making them an absolute dream to wear.


37. A Dr. Scholl's zip-up ankle bootie, because you know this trusted brand — known for its innovative foot comfort technology — will ensure your feet are well cared for.

38. Ankle boots featuring a stylish cut-out design, so you no longer have to choose between looking fashionable and enjoying comfort for your feet.

39. A pair of classic moto boots with buckle detailing and a low heel, so you can look edgy as heck but feel comfy, too. There's nothing edgy about foot pain! You heard it here first!

40. A pair of stiletto boots so you can clickity-clack all along the sidewalk and in the hallways. If you're thinking they're going to hurt your feet, think again. Reviewers say they're comfy and don't even require a break-in period!

41. A pair of platform knee-highs for those ready to embrace the bold Y2K chunky sole trend but worried about comfort. Guess what? Reviewers rave about how comfortable these boots are, even after several hours of wear.

42. Tommy Hilfiger equestrian boots deliver a polished preppy look. With your jeans tucked neatly into these beauties, it’s impossible not to look effortlessly chic. (The truth that you might not feel all that put together will stay between us.)

We've made edits to the reviews in this post to improve readability and ensure clarity.