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When we think of timeless footwear, the ankle boot silhouette instantly comes to mind. And while there are a variety of women’s boots to shop, the best ankle boots for women always top shoppers’ lists year after year. No matter the weather conditions or occasion, ankle booties are a reliable shoe that adds just the right amount of polish to almost every ensemble. Plus, their slight heel, whether block, stiletto, or western-inspired, makes strutting so comfortable. Trust us — these boots were made for walking.
Ankle boots are a wardrobe staple, and no matter which style you choose, it’ll seamlessly fit into your go-to uniforms. You can pair comfortable ankle boots with anything from joggers with a T-shirt to leather pants with a bodysuit, as they look chic dressed up or down. Ankle boots are a foolproof option for any time of the year, and there is no better excuse to refresh your ankle boots lineup now ahead of fall and winter. They even make a great gifts for women, whether it’s her birthday or not (just sayin’).
If you’re looking for a perennial pair of booties, kitten-heeled ankle boots are a major trend for 2023, and have been seen on almost every street style star from Kendall Jenner to Matilda Djerf. Not only are they sophisticated and add a boost of height, their baby heel allows you to comfortably stride around all day without sacrificing style. Alternately, tap into another one of this season’s biggest trends by adding a chunkier style to your accessories arsenal. Women’s combat boots, lace-up designs, and classic Chelsea boot silhouettes are infused in trending ankle boot styles this year, and make the perfect counterpoint to ultra-feminine midi skirts, cozy sweater dresses, or classic denim dresses.
Since all ankle boots are not created equally, we turned to some trusted experts that share their expert-approved ankle boots shopping picks for all different kinds of foot types and needs.
Ankle boots are a timeless silhouette that are constantly being reimagined with fresh ideas and inspiration each season. Fall 2023 is no different, and there are tons of new exciting styles to try to upgrade your bootie rotation.
When searching for your perfect pair, comfort is a key factor to consider, notes Dr. Jackie Sutera, Vionic Innovation Lab Member and New York-based podiatrist. “As a starting point, look for boots that have a cushioned insole with arch support,” she says. “This provides comfort and shock absorption. Also, look for a stacked or a low heel for everyday use. Avoid very flat, or platform-heeled boots as your go-to boots.”
And if you have common foot issues like bunions or hammertoes, Dr. Sutera also advises looking for options with some key features. “People with bunions, wide feet and/or hammertoes should look for styles that can accommodate the forefoot, like materials made of a mesh or a soft, forgiving leather,” she says. “These folks should also avoid toe boxes that are tight, narrow, and pointy.”
She suggests avoiding pairs with thin, flat insoles and outsoles for people who need shoes for plantar fasciitis or shoes for flat feet.
As for plus-size women, who may have wide calves, finding affordable-yet-chic options can be a headache. But thankfully, a range of brands now offer a great selection.
Ankle boots can range in design, but they’re described as a boot that covers the whole foot up to the ankle.
With so many brands in the game, there’s a comfortable and stylish ankle boot for any occasion. Therefore, it’s essential to think closely about where you’re headed because not all ankle boots are created equal, and you want to ensure your pick is the best one for you.
Ankle boots are so versatile that there is no right or wrong way to style them. However, with any trend, we love to look to our favorite celebrities and runway moments to get inspired.
Ankle boots + trousers: Swap your traditional pumps and heeled sandals for ankle boots when heading to work or dinner with friends. Stars like Julianne Hough, Kate Hudson, Selena Gomez, and more were spotted last week in New York City donning these uniforms, proving that it’s one outfit equation to follow. Flat lug-sole ankle boots are a great option to reach for since they’re comfortable but don’t sacrifice style. Mid-height block-heeled boots work, too, since they elongate legs under full-length pants and make any outfit look dressier.
Ankle boots + a dress: If you’re sick of teaming sneakers with your dresses, reach for fun and chic ankle boots. For inspiration, look to Celine’s off-schedule Winter 2023, which showed models rocking edgy ankle boots paired with feminine frocks for a fashionable juxtaposition. Additionally, celebs like Emma Roberts, P!NK, and Naomi Campbell were spotted this month in New York City and Los Angeles sporting high-heeled platform ankle boots. While these shoe choices were statement-making in nature, they instantly amped up simple ensembles with their bold and somewhat daring designs.
Ankle boots + jeans: All jeans can be worn with ankle boots, but your jean silhouette will determine what ankle boot to wear. For example, with skinny jeans, look to a boot with a wide or loose ankle; this way, you can tuck the bottom of the pant into the boot for a sleek look. On the other hand, if you’re working with mom or straight-leg jeans, an ankle boot with a more skin-tight fit will help you achieve the model-off-duty look.
There’s nothing like a fresh pair of boots to kick off fall, and your transitional shopping should always start with an ankle boot. It’s an ideal everyday style you can wear with any outfit no matter where you’re headed. From the office, to brunch, to fun weekend activities outdoors — these comfy booties will keep you striding in style.
Cargo pants and utilitarian-inspired ankle boots: The embrace of cargo pants is here to stay, so why not team them with a utilitarian-inspired ankle boot like a laced-up silhouette? If your cargo pants have an elastic bottom, scrunch them up to the top of the boot; however, if they’re wide or straight-leg, let them rest over the boot, so just the toe pops out.
Cozy sweater dress and black leather ankle boots: A soft wool sweater dress is ideal for the fall time because it keeps you warm enough without a jacket while appearing chic for work or play. A black leather ankle boot is the perfect textural contrast to woven frocks, and shiny hardware like zippers and grommets will play well as built-in jewelry for a throw-on-and-go autumnal outfit.
Midi denim skirt and western-inspired ankle boots: Denim skirts are a major trend for 2023, so why not lean into the Americana aesthetic and opt for a western-inspired style? The hemline allows plenty of room to show of the style, whether you go for snakeskin, leather, or suede, and the block heel will be comfortable for all day wear under heat-insulating denim.
Shearling boots and a leather jacket: Take a style cue from Bella Hadid, who went viral last year for an unexpected ensemble of Mini Uggs and a leather jacket as she stepped out for a slice of pizza in NYC. Her comfort-forward ‘fit centered around a racer leather jacket, vintage tee, and hot pants paired with her low-ankle shearling booties. Mix slipper-like comfort with elevated pieces and play with proportions for an easy-going weekend ensemble.
For more than 75 years, Footwear News has been the shoe authority. Our coverage spans top industry news, retail trends, head-to-toe fashion, athletic and outdoor analysis and more. Footwear News’ global network of editors has carefully curated all product selections featured using our expansive brand knowledge and thorough research to find quality, long-lasting items.
To curate the best ankle boots of 2023, Footwear News editors referenced this year’s fall and winter trends, new retailer releases, and most loved streetwear styles. We compared hundreds of customer reviews in order to find ankle boots with the best fit and feel, as well as tested them ourselves to recommend the best options on the market. We paid special attention to innovative and functional shoe features, from waterproof and heat-insulating materials to convenient slip-on designs.
Dr. Jacquelyn Sutera is an NYC-based surgically trained doctor of podiatric medicine specializing in the prevention and treatment of foot pathology. She graduated from Fordham University with a Bachelor of Science degree in Biology and Philosophy. She later attended the New York College of Podiatric Medicine, where she earned the degree of Doctor of Podiatric Medicine (DPM). She is a proud member and spokesperson for the American Podiatric Medical Association and the New York State Podiatric Medical Society.
Dr. Michael Fishkin is a pedorthist of Northern Illinois Foot & Ankle Specialists.
Dr. Mike Rushton is a Podiatric Surgery Specialist in John Day, OR and has over 25 years of experience in the medical field.
Dr. Neha Pathak is a podiatrist at Pathak Podiatry. She treats patients for a range of common and specialized conditions such as over pronation, bunions, hammertoes, plantar plate injuries, achilles tendonitis, neuromas, ankle sprains and instability. As a former long-distance runner and swimmer, she has a passion for diagnosing and treating sports medicine and dancing-related injuries.
Dr. Mark Mendeszoon is a multi-board certified podiatrist who treats all surgical and non-surgical conditions of the leg, ankle, and foot in both adults and children. He specializes in trauma, sports medicine, diabetic foot and ankle conditions and reconstructive foot and ankle surgery, including Total Ankle Joint Replacement Surgery.
Dr. Alissa Kuizinas, DPM is a Podiatry Specialist in Concord, MA. She currently practices at Concord Foot & Ankle Center and is affiliated with Emerson Hospital. She frequently treats conditions like foot fractures along with other conditions at varying frequencies.
Nikki Chwatt is the Style Commerce Editor at Footwear News and WWD, where she both writes and edits stories on the latest clothing, accessory, and shoe must-haves. As a city dweller, she’s garnered a love for footwear, especially ankle boots, because they’re versatile enough to be worn with any type of outfit and comfortable enough when running uptown, downtown, or cross-town. Therefore, she takes an interest in keeping up with footwear trends and innovations by testing and reviewing shoes in a wide range of categories — from athletic to streetwear styles.
Olivia Cigliano is a Commerce Writer & Producer at Footwear News and WWD where she writes shopping content on the best-rated footwear, TikTok style trends, and more. Olivia received her bachelor’s degree in journalism from Emerson College, and her byline can be found in publications including Elite Daily and CR Fashion Book. In her free time, Olivia can be found scouring the internet for deals on cool combat boots and dad sneakers to add to her ever-growing collection. Cigliano updated this ankle boots shopping guide on August 11, 2023 with the top ankle boot trends for the upcoming fall and winter trends and new trendy ankle boots to shop now. Learn more about us here.
By providing your information, you agree to our Terms of Use and our Privacy Policy. We use vendors that may also process your information to help provide our services. This site is protected by reCAPTCHA Enterprise and the Google Privacy Policy and Terms of Service apply.