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It’s time to strut into fall.
1.
A pair of chunky ankle boots with a whopping 13,000+ reviews and a 4.5 star rating, so you can feel 100% confident in your purchase. The combination of a 3.5″ heel, a pull-on silhouette, and a classic, go-with-anything design.
amazon.com, amazon.com
Promising review: “Obsessed with these boots! They are true to size, comfortable, and so easy to match with so many outfits. They look like they would be expensive boots, the quality is great!” —Paige
Get them from Amazon for $22 (available in sizes 5.5–11 and 10 colors).
2.
A pair of Lucky Brand ankle boots with stylish, side zipper accents that are so cute (and versatile), you won’t be able to stop wearing them. With 40 colors to choose from, you are guaranteed to find one that will fit seamlessly into your wardrobe.
amazon.com, amazon.com
Promising review: “I have had these boots in a different color for at least six years. They are the most comfortable footwear I own. Being stylish is a plus and everyone compliments them. I actually ordered three additional pairs, in different colors.” —Lisa Berns
Get them from Amazon for $67.98+ (available in sizes 5–13, two widths, and forty colors).
3.
A pair of sultry, stiletto boots that are guaranteed to turn heads. I wore these out on a Friday night, and not only did I get a million compliments, but I didn’t have to complain about my feet hurting a single time.
Matisse
I recommend sizing up half a size for the best fit!
Get them from Matisse for $110 (available in sizes 5.5–11 and three colors).
4.
A pair of rubber knee-high rain boots so you can jump into every puddle you see. They are lightweight, weather-resistant, and fortified with anti-slip grooves — and they aren’t agonizing to wear and won’t cut into your feet, unlike many other rain boots.
amazon.com, amazon.com
Promising review: “My wife asked for these as a present. She absolutely loves them. She can’t believe how well they fit and how comfortable they are. She couldn’t stop going on and on about how comfortable they are!” —FuzzyZ
Get them from Amazon for $39.80+ (available in sizes 6–10 and eight colors).
5.
A pair of durable, over-the-knee boots that will look great with everything, from skirts and dresses to jeans and leggings. Thanks to the fact they are made with ultra stretchy fabric, you won’t feel constricted at all, despite their length.
amazon.com, amazon.com
Promising review: “Freaking love these! Purchased for a Vegas trip. And didn’t wear them in before I went. Risky, right? Like never bring a new pair of shoes for a night out. But oh my gosh. They fit amazing in the shoe! And were legit comfortable until 4 a.m. when I got back to my hotel room. Only con: they do slide down a little bit, but nothing terrible, just to the top of my knee if walking. Standing and just moving they stayed up all the way. Just buy the boots!” —Danielle
Get them from Amazon for $48.99 (available in sizes 5–11 and five colors).
6.
A pair of hiking boots because they’re designed to withstand the elements, so you will be prepared for just about anything. They are anti-skid, wear-resistant, water-resistant, AND as cute as can be — what more could you want!?
amazon.com
Promising review: “I wanted some boots to wear when hiking that would get good traction on slippery surfaces. These are great! And I didn’t need to break them in or anything, they were comfortable as soon as I put them on! It goes with everything! I get compliments every time I wear these. I wasn’t really expecting them to be as great as they are. I even wore them on a icy day and they were great! Definitely recommend!” —Natalie Evans
Get them from Amazon for $49.99+ (available in sizes 6–10 and 42 colors).
7.
A pair of Chelsea-inspired, utility boots featuring weighty, durable soles so you never have to worry about tripping. These Seychelles boots — which are a personal favorite of mine — look good with everything, from skirts and dresses to trousers and jeans.
Revolve
I love that these bad boys are a little taller than a usual ankle bootie so I never have to worry about blisters.
Get them from Revolve for $199 (available in sizes 6–10).
8.
Or a pair of Dr. Martens Chelsea boots that will likely last you years, and years, and even more years. These boots, which come in seven different colors, may be a little rigid on your first wear, but trust me, after being broken in, you will feel like you’re walking on Cloud 9.
amazon.com, amazon.com
Promising review: “I’m very satisfied with my purchase. The boots fit true to size and are very soft, light, and comfortable. I’d definitely buy these again and recommend them to anyone wanting a light comfortable boot.” —Cameron
Get them from Amazon for $82.59+ (available in sizes 5–15).
9.
A pair of chunky mid-calf boots with a slight platform that will look amazing with just about any outfit. Reviewers love that even with the added height, they are super easy to walk in.
amazon.com, amazon.com
Promising review: “EXTREMELY comfortable: I am on my feet most of the day, and they don’t complain at all in these. They look just like the photo and are very well made! I usually wear a size 10, which was sold out in the color I wanted, so I purchased an 11 (despite being more on the small side of size 10, generally) and they fit pretty perfectly, so I would say these do run pretty small. I’ve been looking for a pair of Chelsea boots with a fun bright colored sole for ages, and these were definitely the right choice.” —Wrye Mandel
Get them from Amazon for $37.99+ (available in sizes 5–11 and eight colors).
10.
A pair of western boots so you can live your Pinterest fashion girly dreams. Cowboy boots *always* gave me blisters — until I found this holy grail pair from Dirty Laundry.
Dirty Laundry
They’re giving East Village fashion blogger.
Get them from Dirty Laundry for $99.95 (available in sizes 5–11 and three colors).
11.
A pair of quilted knee-high boots with buckle and zipper detailing, for times when you want to walk comfortably with a little bit of throwback preppy style. Plus, thanks to their breathable insoles, this pair will work through fall, winter, AND spring!
amazon.com, amazon.com
Promising review: “I love these boots; they are my go to for events with a lot of walking or standing. They have grip soles so perfect in winter, plus they are fashionable! Love, love, love them!” —Jae
Get them from Amazon for $69.99+ (available in sizes 5.5–11 and 12 colors).
12.
A pair of classic, easy-to-slip-on, mini Ugg boots that will likely become your go-to pair of shoes this winter. Since these boots are lined with sheepskin, they are sure to keep your feet warm, no matter how low the temperature drops.
amazon.com
Promising review: “I love these boots so much, I don’t want to take them off! Feels like I’m walking on a soft rabbit carpet. Some have commented that they can’t get their foot in. I definitely need to use the hook on the back to pull my feet into them, but it’s no problem. I walked 4 miles outside in the cold with these boots on yesterday, and my feet don’t hurt at all, and I stayed cozy and warm. I’m glad I finally broke down and bought these. I’d been shopping for awhile and seen them for ~ $150. The local shoe store told me they’re not allowed to go on sale per the manufacturer, so I was thrilled to find these for $99 at Amazon. Also, this style is short enough that you can either tuck your pants in or wear them over the boots.” —Islandgal
Get them from Amazon for $159.95+ (available in sizes 5–12 and 20 colors).
13.
A pair of slouchy, mid-calf zip-up flat boots, for the days where even a kitten heel feels like too much. Oh, and since they are nonslip, you will be good to go even when the weather turns.
14.
A pair of suede Dolce Vita boots with asymmetrical color blocking that will simultaneously go with everything and *still* stand out. Reviewers recommend sizing up for a walk-until-you-drop fit.
Dolce Vita
Promising review: “I went back and forth on ordering these. I am so glad I did. They are so cute! I am between a 7.5 and 8 and ordered the 8. They fit perfectly! I may order in the darker shade; I like them so much! I got the lighter nude tones, and they are so pretty!” —Jamie S.
Get them from Dolce Vita for $175 (available in sizes 5–13 and three colors).
15.
A pair of stylish ankle booties because they effortlessly combine a classic Western feel with a city modern silhouette, with their short, chunky heel, trendy ankle slit, and back zipper.
amazon.com
Promising review: “ These are the perfect booties and exactly what I was looking for. They are comfortable and cute!” —Lilli
Get them from Amazon for $51.11+ (available in sizes 5–11 and five colors).
16.
A pair of ultra-fun boots with a chunky block heel, so you can feel like a badass every time you put them on. Despite having a bold pattern, the neutral colors makes them perfect for mixing and matching with a variety of outfits.
amazon.com, amazon.com
Promising review: “I wore them for 6 1/2 hours and walked all downtown with zero problems, I got so many compliments on them. They are comfortable, stylish and exactly what I needed.” —Gabriella Ann
Get them from Amazon for $59.99+ (available in 14 styles).
17.
A pair of knee high boots with a side zipper that I am pretty sure were created with the sole purpose of strutting your stuff.
Amazon
Promising review: “The fit is great, very comfortable and I get complimented on them all the time! Love these boots!!” —Wendi
Get them from Amazon for $89.99+ (available in sizes 5–11 and nine colors).
18.
A pair of sparkly ankle boots, because sometimes, you just want to wear a literal disco ball. These Betsey Johnson shoes are a must-buy for anyone who loves a little glitz and glam — they’ll absolutely be compliment magnets, wherever you go.
amazon.com, amazon.com
Promising review: “I bought these for an Elton John concert and received so many compliments on them throughout the evening! The rhinestones are absolutely stunning and even though I don’t wear heels often I was able to comfortably wear these for several hours. However, I would highly recommend going up a half size! I read several other reviews recommending this and am glad I did or else they probably would not have fit. I’d recommend going a half size up from your regular shoe size, but otherwise these boots are perfection!” —Amazon Customer
Get them from Amazon for $114+ (available in sizes 5–11 and 19 colors)
19.
A pair of ankle boots with soft, synthetic outsoles, so you can wear them for hours on end. Available in black, burgundy, and caramel, these ultra-comfy boots have a round toe, criss cross straps, buckle hardware, and a low heel — so you’ll look like you’re on the cutting edge of fashion, but feel like you’re wearing your fave broken-in sneakers.
Amazon
Promising review: “You can’t go wrong with Clark shoes. I’m very happy with the comfort and fit. Heels are perfect height … not low and definitely not too high ….highly recommend!” —Louise
Get them from Amazon for $92.85+ (available in sizes 6–11 and three colors)
20.
A pair of mid-calf, lace-up boots featuring a platform, rubber sole, loafer-inspired detailing, and zipper closure. Comfy enough for all-day wear and cute enough for every outfit, these are a must-have in your wardrobe.
Free People
Promising review: “Love these. The quality is phenomenal. Much prettier in person. Had to exchange for a half size smaller because they are a little big, but all in all a great boot. Looking forward to wearing it with dresses and skirts.” —Amie L.
Get them from Free People for $198 (available in sizes 6–11 and four colors).
The reviews for this post have been edited for length and clarity.
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