9 Editors Tested & Found the Best Ankle Boots—Here Are the 25 Pairs We Recommend

Sizes: 5-12 (including half sizes)
Colorways: 2 

“I’ve always been a Steve Madden girlie. The brand has always delivered when it comes to quality on a budget. Through the years, however, I realized that I’ve never tried a pair of Steve Madden boots—only heels and flat sandals. When I saw the Shayne White Leather Boots, I knew I had to have them. As a Southerner, I’m always down with the Western aesthetic but this year (thanks to Beyoncé) country attire is hotter than ever. I wanted something that felt trendy but timeless, and I liked that these were a bit more subtle than the average cowboy boot. The white also feels unique and funky. I knew I wanted to pair these with denim, either my Jaded London jorts or my Free People barrel jeans. I landed on the barrel jeans and built my outfit from there. Since both the pants and the boots felt very country, I added contrast with a blazer from Banana Republic and a bodysuit from Zara. The outfit felt retro but so very chic. I wore this on a Sunday for a day out in the city with my best friend, and the look was a hit. The boots felt sturdy and they fit true to size. After a while, my feet did start to hurt because the toe area is a bit tight due to the pointed construction, so I don’t recommend wearing these if you’re going to be walking around for hours. All in all, I am obsessed with these, and I can’t wait to style them this winter with a statement coat.” — Robyn Merrett, Style & Beauty Editor

Sizes: 5-12 (no half sizes)
Colorways: 2

“I’ve always wanted these Church Platform Monkey Boots, and I’m glad I finally got them. I’m an avid Dr. Martens wearer, so I thought this pair would run a half size big like the rest of my Docs do—but I was very wrong. Instead, I’d say these run at least a size and a half bigger. Once I got the correct sizing, I couldn’t get enough of these boots. They’re like my other Docs in the sense that they go with practically any outfit, but at the same time—they’re unlike any other shoes in my collection. They have a preppy yet edgy vibe, which is perfect for skirts and dresses. I adore the yellow stitching throughout and the chunky platform sole was right up my alley. I can see myself wearing these for years to come, because like most Docs, they’re high quality and feel super durable. I might even bust these out once it starts snowing.” — Kleigh Balugo, Trending Beauty Writer

Sizes: 5-13 (including half sizes)
Colorways: 2

“Oooo girl these are cute. I thought I was late to join the cowgirl boot trend when everyone and their mothers were wearing them last summer, but I decided to get a pair for fall, and I received so many compliments! People usually gravitate toward cowgirl boots with high shafts, but I think the ankle boot length was super breathable and easier to walk in. I’m wearing a size 9 (I half-sized up), and they’re perfect. The material is suede, which surprised me, but I thought they’d stand out from leather. The only thing I have a slight issue with is the toes got a pit scratched up from walking, but hey, what can you do? Not walk? I, of course, had to wear them with a denim-on-denim Canadian Tux fit. My shacket (cool word for a shirt/jacket) was belted at the waist, and my denim shorts were a pair of thrifted jeans that I took a pair of scissors to. 1,000/10.” — Kaili JiMei, Social Media Manager

Sizes: 5-12 (no half sizes)
Colorways: 3

“By far, the comfiest boots I have ever worn since my childhood. As someone who’s lived in New York for the longest time, my biggest fear is falling on the ground really hard. I mean I’ve done it so many times, but I feel like heels are the main culprit here. That’s why I’ve been avoiding heeled boots for the longest time. These boots make me feel really stabilized with their light and hollow heels that still shine with a metallic glaze. The leather wraps around the top of my foot like a feather it feels like I’m walking on absolutely nothing. Am I still afraid of falling? Perhaps, but maybe these shoes could be training wheels for wearing some taller boots.” — Lea Veloso, Entertainment Writer

Sizes: 5-12 (including half sizes)
Colorways: 4
Widths: Medium, Wide

“Out of all the boots I called in and wear-tested, Naturalizer’s Deesha Bootie comes out on top in terms of comfort, and I find myself reaching for this pair the most. I’m still in utter shock at how well they support my feet as I fast walk through bustling New York City. I’m in love with the Chocolate Bar colorway and think it’s the perfect, most fall-ready color you could ask for. As for sizing, I’d suggest sticking to your usual size—no need to size up or down. Styling note: I usually wear them peeking out of baggy jeans or trousers.” — Katie Decker-Jacoby, Associate E-commerce Editor

Sizes: 5-13 (including half sizes)
Colorways: 4

“If you love kitten heels, you NEED these. I’ve always wanted a pointed-toe ankle boot with a super sharp toe, and these are the ones. My only complaint is by the end of the day (day as in 20-minute walk to work, work, and 20-minute walk back from work), the pointed part was a bit scratched up. I’m sure the best practice would’ve been to treat the leather with some sort of protector. Oops. However, I will be wearing them again. I should also add that because the heel is so low, you don’t feel like you’re walking in heels at all! They almost feel like you’re walking in flats. I could walk at my normal fast NYC streets pace. The dark brown leather matches so many belts and gives the look such a clean, polished feel. It’s sweater weather, so you know I paired these with my ride-or-die Madewell jeans and $12 striped sweater from H&M.” — Kaili JiMei, Social Media Manager

Sizes: 5-12 (no half sizes)
Colorways: 4

“I had always wondered if skinny, sculpted, low heels were comfortable because I assumed it was a no. However, the Justine Ankle Boot proved that this height and shape of heel might be the way to go if you’re after heeled boots that won’t snap your ankles in half. In fact, I wish I had discovered this sooner! Perhaps it’s these shoes’ MWL Cloudlift Lite padding that makes them so special and a total breeze to walk in. I wore them to and from the office—including an off-site work happy hour—and didn’t stumble in the slightest. In a place like New York City (AKA stairs galore, uneven ground, and trash everywhere), that’s a huge feat.

While these boots cost more than $200, I say they’re definitely worth the investment because of their comfort and versatility. For fit, I sized up to a 6.5 (I’m usually a 6) because of the slimmer design, and thank goodness I did because they’re perfect.” — Katie Decker-Jacoby, Associate E-commerce Editor

Sizes: 5-11 (including half sizes)
Colorways: 3

“These Sarto Flexa Fabiene Booties are so beautiful; they really are a work of art. I ordered them in 9.5, which is my exact shoe size, and they fit perfectly. I got them in Berry Red Leather, which is a gorgeous mix of dark chocolate and burgundy that radiates autumn warmth with each step you take.

I love that the leather—which is responsibly sourced—is so soft and smooth, but also durable. The block heels are two-inches tall, which gives you a nice, but subtle lift. The heels are also adorned with a tiny gold sigil that makes them feel unique and ever-so-slightly decorated. Putting them on is a very easy process, as my feet slide right on and the zipper moves in a fast and fluid motion. The square toe makes these boots look so chic and elevated, reminding me of all the Franco Sarto boots my super fashionable mom used to wear during the 90s (my favorite decade for fashion). I love to wear these with leggings, pants, or jeans, but they also look awesome with skirts and dresses. If your outfit is made up of mostly neutral tones, you could wear these boots to add a subtle pop of warm color. They’re especially fun to wear when you’re walking on a sidewalk covered in crunchy autumn leaves!” — Roya Backlund, Astrology & Lifestyle Editor

Sizes: 5-11 (no half sizes)
Colorways: 2

“Can I just say that these are the most badass shoes I’ve ever worn in my life? I am a Doc Martens devotee and will wear them to any occasion, but I will bring out these boots for the big functions. Like any Docs, they will take A LOT of time to break in, but the style is worth it. I love how the boots have a flair of color splattered across them instead of it being monochrome. The platform also gives it a huge bonus because it makes me strut confidently at a concert and as a short 5’2 person, it helps me become a tall figure. It’s a unique addition to my closet and I love getting compliments on them. It makes the pain of breaking them in worth it.” — Lea Veloso, Entertainment Writer

Sizes: 5-11 (including half sizes)
Colorways: 3

“The Lasko Bootie was the first shoe I tested for this story and got me off to a very strong start. I told my coworkers I kept forgetting that I was wearing heels with these on—they’re just that easy to walk in, light, and cushioned. I literally think I could run in these heeled boots and not miss a beat. I owe the Ortholite Aerofly foam insoles and diamond flex soles all the credit here.

As for the color, I always stay on the safe side with neutral-toned shoes, but something about this bright red pop of color spoke to me. I took a leap of faith with these boots and am so glad I did. They match perfectly with my tiny red bow clips (pictured above)!

I’d suggest going a half size up (I’m typically a 6, but got a 6.5), since this shoe is kind of like a sock boot (AKA hugs your ankle tighter).” — Katie Decker-Jacoby, Associate E-commerce Editor

Sizes: 5-12 (including half sizes)
Colorways: 2 

“I was immediately drawn to the Pia Chestnut Suede boots because the color looked so rich, and suede is ‘it’ this fall. Everyone’s trying to get their hands on suede accessories, so I felt this was the perfect time to go for a suede shoe. The square toe and fold-over construction (which was big on a few spring/summer 2025 runways) also felt eye-catching and unique. When I got them in the mail, they were exactly how they were pictured on the site. I decided to take them out on the town during a trip to Austin, Texas, pairing them with a strapless denim dress from Zara. The pairing felt so cohesive. Rugged but chic. I was worried that they would be uncomfortable and hard, but they felt fine—though I was only in them for a couple of hours and I was seated for the majority of that time. They did feel a bit heavier than I thought they would be, so I don’t recommend these if you’re going to be on your feet all day. All in all, I loved the quality. They completed my look perfectly, and I got tons of compliments!” — Robyn Merrett, Style & Beauty Editor

Sizes: 5-12 (no half sizes)
Colorways: 3

“I was so excited when I pulled these Jully Metallic Trapeze Heel Ankle Boots out of the box. I normally wear a 9.5, but this brand does not offer half sizes, so I sized up to a 10, which fits my long and narrow feet perfectly. However, there is still a bit of space for those who have somewhat wider feet, and the material does provide a slight stretch. I got them in Chalk, which is a creamy neutral white that reminds me of the color of vanilla ice cream.

I love that the material—a natural vegan leather—is very smooth and flexible, but the boots also feel sturdy, like I could run in them or stand in them for hours. They’re super easy to put on; just slide your foot in, zip up, and voila! I love the metallic gold trapeze block heel, which is a subtle, but glamorous detail that adds a touch of elegance to the look. Whenever you turn, sunlight catches on the gold heel, giving your outfit a little something extra. I love wearing these with a mini dress or a pair of flare pants. It feels like a modern twist on the 1960s go-go boot look. The best part? They’re super comfortable and required no breaking in, which is amazing considering the affordable price point. They’re also very lightweight and the rounded toes allow your feet to spread out comfortably.” — Roya Backlund, Astrology & Lifestyle Editor

Sizes: 5-12 (including half sizes)
Colorways: 4
Widths: Medium, Wide

“You have to admit, anything with a kitten-heel is automatically chic. Sadly, most of the time, they aren’t very comfortable. Yet, these booties from Naturalizer went above my expectations and surprised me with how comfortable they are. Not only am I able to walk up and down subway platform stairs without any problems, but I can easily slip them on and off with the boot’s useful zipper. I will say that my usual size fits slightly snug, so wearing a thin sock or tights underneath would be the way to go. (Wearing a thicker sock didn’t let me zip the boot up all the way.) Plus, the chocolate brown color is beautiful and perfect for fall. For their price, fit, and look, these are totally worth the investment.” — Jennifer Adams, Lifestyle Writer

Sizes: 6-10 (no half sizes)
Colorways: 3

“I’ve oftentimes found myself a victim to wearing uncomfortable ankle boots. Whether it be months of “breaking in” or endless awkward band-aids, ankle boots are the complicated main character I don’t really want to get to know. 

When I first got my Quince boots, I was worried about the material. To no surprise, putting on these waterproof boots felt like I was a coastal fisherman about to command a lighthouse during a hurricane. As a self-diagnosed sweaty person, sweating inside a rubber shoe does not conjure the most exciting feeling. Thankfully, between walking from the train to sitting in a temperature-indeterminate office, these boots felt breathable throughout the day. 

These boots come in three colors, I ordered mine in BRAT [green heart emoji]-but-it’s-not-really-but-still-BRAT green (a.k.a  “olive”). I’d still practice caution if you find your feet heat-averse and avoid thick socks.” — Stephanie Cui, Graphic Designer

Sizes: 5-11 (including half sizes)
Colorways: 3

“I love a good Western boot moment and have been trying to find a pair that isn’t necessarily a full-on cowboy boot but isn’t a short bootie. Everlane’s Outlaw Boot is the perfect in-between and can help bring so much sophistication and sass to any outfit. And while the block heel is nearly 3 inches, these shoes remain comfortable enough to strut in all day. My regular size 6 did the trick, although my coworker, Kaili, did notice that the boot’s ankle region fits a tad narrow for her.” — Katie Decker-Jacoby, Associate E-commerce Editor

Sizes: 5-12 (including half sizes)
Colorways: 2
Widths: Medium, Wide

“I was first intro-ed to Naturalizer when I was getting ready to study abroad in France. I needed comfortable (and stylish) shoes that I could walk everywhere in. Naturalizer didn’t do be dirty in 2019, and they definitely aren’t doing me dirty in 2024. I bought my Aimee ankle boots in half a size up (I’m wearing a women’s 9) because my mother always told me to size up in boots to make room for your socks.  They fit perfectly, feel great, and the block heel kept me balanced during my outing all over the Plaza, Kansas City’s gorgeous outdoor shopping mall. I love wearing boots with my wide-leg jeans from Madewell, and I paired them with a really nice knit sweater. Oh, and a bonus: these bad boys are “weatherproof,” which means they’ll be perfect to still wear when it starts snowing this winter.” — Kaili JiMei, Social Media Manager

Sizes: 5-11 (no half sizes)
Colorways: 4

“I recently got my first pair of Uggs and I couldn’t get enough of them. So, I decided I need a pink platform pair in my life. As the weather grows colder, I know these will be my go-to to keep my feet nice and warm. Just like my Classic Short Uggs, these run pretty true to size—and I like wearing them with a thick pair of socks on days when I need extra warmth. Surprisingly enough, these have been pretty easy to style. The platform sole makes them perfect to wear with bootcut jeans, which is my favorite combination for a cute and cozy fall outfit. At first, I felt like they almost looked like mascot shoes because of how chunky and pink they are, but I soon realized how much I love them. They’re almost like a more subtle version of Moon Boots. They’re the perfect pop of pink my wardrobe has been desperately needing, so I can’t wait to come up with new outfit combinations.” — Kleigh Balugo, Trending Beauty Writer

Sizes: 6.5-11 (including half sizes)
Colorways: 2

“I went a little out of my comfort zone with the Palomina Boot, as it’s not a style I’d usually go for. However, I’m always game for a chunky shoe. This pair was a pleasant surprise, with its faded grey colorway (no longer available, sadly) initially sealing the deal for me. I’m thrilled that I get an extra 2.5 inches to my height when I wear these shoes and can definitely last all day in them without feeling any discomfort. One thing to note is that I would recommend sizing down. I got a 6.5 and wish I had stuck with my true-to-size 6 because they feel roomier than I’d like.” — Katie Decker-Jacoby, Associate E-commerce Editor

Sizes: 3.5-14 (including half sizes)
Colorways: 2 
Widths: Medium, Narrow, Wide

“As someone who wears jeans nearly every day, I’ve been in search of ways to elevate my daily, casual look while still staying comfortable. I can officially say that The Agnes Boot is what I’ve been looking for. The shape—along with every other feature of the boot—is perfect. I love it because the narrow, pointed toe and block heel hint at a western, cowboy boot without being over the top. It adds some personality to a plain t-shirt and bootcut jeans, making these boots a true staple in my closet. Aside from the boot’s look, I was also surprised at how comfortable these were. I was initially a little skeptical because any pair of heels (no matter their height) always hurt my feet, but these made my feet feel great after a full day’s wear. 10/10 obsessed.” — Jennifer Adams, Lifestyle Writer

Sizes: 5-13 (including half sizes)
Colorways: 3
Widths: Standard, Wide

“When my pair of Saline H2O Booties arrived, they looked just like the picture on the website. I ordered a 9.5, which is my exact shoe size, and these boots fit like a glove. I got them in Midnight Crinkle Patent, which is a super dark blue that almost looks black, but the bluish hue makes it appear more vibrant.

I was able to do a full day of shopping in these bad boys, and they didn’t even need breaking in. Normally, I gain a few blisters when I wear a brand new pair of shoes all day, but these boots were comfy from beginning to end. They’re super easy to wear, they just slide right on. They also feel very sturdy and the heel is substantial, but not too heavy. I love how they’re edgy and chic—a perfect set of boots to pair with my skinny black velvet leggings. However, they also have a knit upper that adds a soft and cozy vibe to the look. My dream is to wear these boots during my next trip to Sweden, as it reminds me of what the stylish Scandinavian girlies wear during winter. You can pair these with thick socks and stay warm during the cold months. While I haven’t worn these in the rain yet, I did step in a puddle and they dried right off. You would never have known they got wet!” — Roya Backlund, Astrology & Lifestyle Editor

Sizes: 5-11 (including half sizes)
Colorways: 4

“When I was deciding on which ankle boots to try, I was immediately drawn to the Dasia boots. Between Mitski, Kacey Musgraves, and Urban Decay’s bestselling eyeshadow “Space Cowboy”, everyone should occasionally be the proverbial “cowboy”. 

One of the first things you’ll notice is the quality. These boots really give that “person in business” clack on every surface you walk on. Despite how domineering these boots may sound, the flexible interior construction truly emphasizes comfort in long-term wear. 

If you’re a non-believer in aesthetic commitment, these ankle boots are perfect if you want to incorporate a sense of pseudo-western flair into your everyday. I’d recommend getting a size up if you like wearing thick or slouched socks.” — Stephanie Cui, Graphic Designer

Sizes: 5-11 (including half sizes)
Colorways: 3

“When I added these to cart, I didn’t realize they had cutouts, so I was a bit taken back when I tried them on. I didn’t think I was grunge (??) enough to pull them off. Then I remembered my co-worker, Katie—a.k.a. the one who orchestrated this entire article—wore a long white dress with chunky black boots, and she looked so cute! For styling, I just copied and pasted her look. I think the cutouts with the buckles give my outfit an unexpected edge. I ordered a size 9, as a regular 8.5 wearer. I was afraid they would rub and blister the sides of my leg, but all was OK. This was the perfect look for a fall dinner with friends.” — Kaili JiMei, Social Media Manager

Sizes: 3.5-14 (including half sizes)
Colorways: 2
Widths: Medium, Narrow, Wide

“I was ridiculously excited to receive The Skater Boot by Margaux in the mail and I kept checking the tracking number until it arrived. Fortunately, they did not disappoint and they’re even more beautiful in person. Even though these come with a hefty price tag, these are some extremely well-made boots, and you will absolutely get your money’s worth. I ordered them in 9.5, which is my exact size, and they fit like they were made for me. They’re a little bit roomy because they’re designed to be worn with thick or heavy socks. If you want to wear them with thinner socks, you should go one half-size down. I also got them in Deep Royal Suede, which is a super dark blue that’s almost black, like the ocean at night.


Designed to be worn in the wild as well as the city, these are an extremely fashionable, yet versatile pair of boots. I packed them for a vacation to Big Bear, California and loved wearing them for nature walks. I also wore them to a Charli XCX concert and they held up all night, looking super fashionable with my all-black getup. Every single part of these boots is waterproof—even the German suede—and during the concert, someone spilled their drink on them, but the liquid rolled right off the fabric like it never happened.

They come with hooks that make it easy for you to lace them all the way up. If you hate it when your laces drag on the ground, all you have to do is simply loop them through the leather hook at the back of the boot and tie them in front for a tight and pulled-together look. I also really loved the way the top edges of these boots are cushioned, making these shoes extra soft around your lower legs and ankles. The rubber lug sole is also very durable and allows you to gain traction on slippery surfaces, like a garage floor or a linoleum floor. I’m a grade-A klutz, and I’m happy to report I’ve worn these several times and haven’t slipped once!” — Roya Backlund, Astrology & Lifestyle Editor

Sizes: 5-11 (no half sizes)
Colorways: 1

“I’ve had Dr. Martens boots at several points in my life and there’s a reason I keep coming back to them (I’m pretty sure my last pair got lost in my move from Australia to New York). They’re so solidly constructed and while previous versions I’ve owned have been stiff and a bit difficult to break in, these feature soft Nappa leather panels at the front, so they’re comfortable from the very first wear, even after a whole day trudging to and from the subway and around midtown Manhattan. 

Because the temperature in NY has dropped rather suddenly, I’ve been wearing these with jeans mostly, but in the warmer months, these would pair excellently with a shirt dress or something a little more flouncy and fun.” — Sophie Hanson, former Entertainment Editor

Sizes: 3.5-14 (including half sizes)
Colorways: 1
Widths: Medium, Narrow, Wide

“Living in NYC, I walk at least 10,000 steps daily, so I’m always in search of a comfortable shoe. While I love wearing my casual, athletic shoes, I’ve also been looking for a nicer, elevated shoe to wear to dinner or in the office. It’s difficult to find a pair of pretty boots that don’t sacrifice comfort, but I feel like I’ve won the shoe lottery with these. They’re the most comfortable and elegant pair of boots, ever. I’ve walked several miles in these boots and they didn’t ever give me blisters. They feel like you’re walking on a padded pillow, so I’m confident that these are also the perfect shoes for travel. Plus, the leather looks so expensive and nice, and always gets me compliments.” — Jennifer Adams, Lifestyle Writer