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Chunky wedge booties, here we come.
Unless otherwise specified, all sizes in this post are listed in women’s.
1. Steve Madden ankle boots available in striking but still neutral hues and fun finishes, like fur trim and suede. Their out-of-the-box comfort are just an added perk.
2. Tommy Hilfiger equestrian boots which remind me of Massie Block (and her described style) from The Clique series and I mean that as the highest possible compliment.
Promising reviews: “This is my second pair. The first pair which are black, was brought years ago and they still look great. I can’t wait to wear these!” —Cheryl Jones
“I have been looking for quite some time for black boots. I took a chance on these and went by what the reviews said. When I tried them on the first time and wore them, they were so comfortable. I really can walk in them for hours, and my feet do not hurt. They are so worth the money and very stylish. I do have a wide calf (16 inches), and there is plenty of room. I highly recommend these boots.” —Fotodiva
Price: $69.94+ (available in sizes 5.5–12 and six colors)
3. Platform Chelsea boots to chic-ify (that’s a real word, look it up) pretty much any look: mini skirts and sweaters, skinny jeans and white crewnecks, etcetera.
Promising review: “I was surprised how great of a boot these are for what I paid for them. Great quality and I lasted walking for several hours in Europe in them without my feet aching. They protected my feet from snow, rain, and ice too. I never had any slip issues when walking in ice or snow which was great!” —Amanda Irvin
Price: $30.99+ (available in sizes 5–11 and in four colors)
4. Western-style ankle boots to take any look from 0 to chic. Blue jeans, white tee, tight bun combo — meet the shoes that are about to tie your whole look together.
5. Sorel boots constructed with faux-shearling insoles and a waterproof outer, meaning they’re comfortable enough for long commutes and won’t fall apart in the event of an unexpected rainstorm.
Promising review: “These boots are so comfy and warm! There’s no breaking-in period. They fit like high-top tennis shoes. I’m normally a size 6 but had to go with size 7. They are super cute!” —DealTracker
Price: $91.92+ (available in sizes 6–11 and six colors)
6. Kitten heel boots proving you *should* dress for the job you want. Job in this context? CEO of a cool creative company that (fill in your personal mission statement here). These shoes are your one-way ticket.
Promising review: “I usually wear heels for pictures only and change into flats immediately after lol. I just refuse to be uncomfortable. These were perfectttt for me… cute and super comfy!! I wore them to my birthday party and kept them on alllll night (I even did a few line dances in them and my feet had no pain).” —Nae
Price: $72.99+ (available in sizes 6–10 and in 10 colors)
7. Faux crocodile knee-high boots that, despite having a generous heel, are comfortable enough to walk around in all darn day (and/or dance in all night long).
Promising review: “These boots were so comfortable and BEAUTIFUL. I walked around NYC for several days in a row in these boots with no issues. The black glossy crocodile is stunning. I got so many compliments on them. For the price, they are a great value and seem like great quality. I love the toe shape with the thick heel…very in! They fit perfectly.” —Libby Patterson
Price: $59.48+ (available in sizes 6–11 and five colors)
8. Chelsea boots that are *the* epitome of fall. Pair this with blue denim, a cardigan, and/or a plaid shirt, and boom — you’ve been transported to 2013 fashion Tumblr (in a good way).
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
Price: $34.99 (available in sizes 5–11 and in nine colors)
9. A chunky ankle boot that should really start negotiating for PTO now, considering you’ll likely wear them every darn day. These babies are destined to become the ~little black dress~ of your shoe collection.
Promising review: “I love everything about these boots. They are well made, very fashionable, and comfortable. I was a little concerned about the height of the heel being uncomfortable but I wore them to work all day and didn’t have any problems with my feet hurting. Very happy with my purchase!” —momtojsh
Price: $42.95 (available in sizes 5.5–11, including wide fits, and 11 colors)
10. Chic London Fog rain booties that have me contemplating a cross-country move to Seattle, Washington for an excuse to don these daily. All I want do is wear. these. boots. and jump! in! puddles!
Promising review: “I brought these to DC for a wet weekend of sightseeing. Though tennis shoes would be the best option for the amount of walking we did, these were suitably comfortable and kept my feet dry for all seven plus miles we walked that day. (Not to mention how absolutely adorable they are!) No blisters, no regrets!” —RT
Price: $44.95+ (available in sizes 6–11 and 18 colors and patterns)
11. Tie-back thigh-high heeled boots I highly recommend pairing with a mini skirt and cozy sweater. The outcome will be *chefs kiss* and I bet you already have something similar saved to your Pinterest board. Prove me wrong.
Promising review: “THESE ARE THE BEST BOOTS! True to size. Great heel height as well as thigh height. I am 5’9 and they come above my knee just enough to have the over-the-knee look! Super comfy to walk in and have a great faux suede texture! Highly recommend these boots! I have the burgundy, black, and tan/khaki now!” —RL
Price: $39.99+ (available in sizes 5–11 and 10 colors)
12. Western boots I’d argue are better than a roundtrip ticket to Nashville (no security lines, no having to pay for a carry-on at the gate, etc.). A comfortable, chunky heel coupled with jersey lining, an anti-skid sole, and pull tabs make these knee-highs a dream.
amazon.com, Amazon
Promising review: “These boots are great! Very comfortable. I have thick calves and they fit great, not tight at all. They stay up and don’t slouch, so they keep their shape well. I am a mama of very active children, and these boots are perfect for when I want to look a little more put together and not have to worry about them getting scuffed and costing me a lot of $$$. Great to wear casual or dressed up.” —Amazon Customer
Price: $65.99 (available in sizes 6–11 and in eight colors)
13. Thigh-high boots that are the perfect compromise: They look ultra-dressy but manage to be unbelievably comfortable, ergo you can look chic and put together without having to feel like you’re wobbling around on stilts.
Promising review: “I decided to give these a try because of price, and I’m so glad I did! I was very impressed by the quality of the material, as well as how comfortable they are. I am very picky about my shoes and typically do not buy shoes that are not name brand.” —Whitney
Price: $42.99+ (available in sizes 5.5–11 and in 19 colors)
14. Hiking boots because they’re making me, a non-winter person, excited for the dreary months ahead. These fleece-lined shoes are the shoe equivalent of a Hallmark movie, hot chocolate, and a mystery novel that TikTok elitists would call “poorly written” — in other words, the epitome of cozy.
Amazon
Promising review: “These boots are amazing. The fit is extremely comfortable with no pinching. They’re the most stylish fall and winter boot I’ve ever had. The shearling and material are textured and rich and it’s easy to tie the laces. Love love love them.” —Lorelei O’Hagan
Price: $66.59+ (available in sizes 5–13 and four colors)
15. Cozy slip-on booties equipped with a chunky heel and fuzzy inner lining for comfort, plus an adjustable shaft that basically means you’ll be purchasing *two* pairs of adorable shoes for the price of one.
Amazon
Promising review: “In fact, I have them on right now. I am always hesitant about ordering shoes online. Not sure how they will fit. Or how they will look. But I SO loved the look of these, so I risked it. They are so so comfortable. They look FABULOUS! And I love that they aren’t noisy when I walk around. They are very very quiet.” —Jaya
Price: $61.99 (available in sizes 4.5–11 and six colors)
16. Microsuede ankle booties guaranteed to become part of your daily uniform due to how comfy, versatile, and stylish they are. *screams cha-ching when thinking about owning these boots*
Promising review: “Yesss. I was looking to replace a far more expensive pair of boots (I wear a size 12). I’m so surprised at the look and fit of these shoes. Nailed it, Amazon!” —Allison Buck
Price: $38+ (available in sizes 5–13 and four colors)
17. Dr. Scholl’s wedge booties equipped with a memory foam, cushiony insole so that you could hypothetically walk 500 miles (and perhaps 500 more) without experiencing any discomfort. Not all heroes wear capes.
Promising review: “I LOVE these boots. They’re so soft and comfortable, I don’t ever want to wear another pair of heeled shoes! I got the taupe and now I want them in the darker brown, too! Who knew Dr. Scholl’s even made such cute shoes?!” —Chelsey
Price: $49.99 (available in sizes 5–11, including wide fits, and three colors)
18. Columbia hiking boots because perfection really does exist, and it’s both stylish *and* functional. Reviewers can’t stop raving about the solid quality, out-of-the-box comfort, and excellent traction that these waterproof babies offer.
Psst, most reviewers recommend ordering a half size up!
Promising review: “These shoes are phenomenal. The lacing holds tight, so if I wear light socks, my foot doesn’t shift. However, there’s plenty of room to wear wool or fluffier socks. For me, they DID NOT NEED BREAKING IN. This is huge. I hate buying any kind of shoe that has a ‘breaking-in period.’ These were great from the get-go. I tried them on a moderate 5-mile hike on a rugged Washington (state) trail. No blisters. I put them to the test today on an 8-mile hike up a steep incline, and holy cow. They were amazing.” —Stevie
Price: $69 (available in sizes 5–12, including wide fits, and 20 colors)
19. 100% leather Chelsea boots brought to you by Dr. Martens for comfy-but-make-it-badass rocker style. These are lined with faux fur to keep your hooves warm and toasty.
Promising review: “I found out I had to spend two weeks in Europe during the winter and ordered these in a pinch. Best. Decision. Ever! They are comfortable, warm, and weatherproof. They survived the snow, ice, and rain. They are also very easy to dress up and down.” —Mari
Price: $108 (available in sizes 5–14 and in 103 colors)
20. Kamik waterproof boots you can drag through snow, sleet, rain, and mud, but rest assured that your hooves will remain perfectly warm and dry. These are fantastic for the colder months, plus great for hiking rough terrain.
21. Square-toe boots guaranteed to become your new “it.” And by “it,” I mean this is your new official go-to shoe — the kind of gorgeous thing that pulls through when you have five minutes to get ready, a white crewneck, high-waisted jeans, dirty hair, and no patience.
Amazon, amazon.com
Promising review: “Very comfy and great-looking boots! Just like the picture. The heel height makes me taller but isn’t too steep to walk naturally. The zipper is smooth to pull up, and it stays up and doesn’t creep down over time. Overall, very happy with this purchase.” —Rebecca Henry
Price: $74.90+ (available in sizes 5–13 and in five colors)
Reviews have been edited for length and/or clarity.
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