Ankle boots — the ubiquitous fall mainstay in our closets can be worn year-round thanks to their timeless aesthetic and versatility. They add warmth and comfort to our feet and can be styled with multiple ensembles. Plus, what else pairs so perfectly with your entire seasonal wardrobe of cozy knits, plaid and denim?
With so many variations in the retail space, ankle boots can be high or low, chunky or sleek and even feature intricate details. Fashion experts break down the styles to own this season along with tips on how to properly wear them.
And if you're wondering if ankle boots are age-appropriate, you can ask my mom (a woman in her 50s), who steals all my samples.
Best slouchy ankle boots$29.99$99.00
Features to look for in ankle boots
Before you go shopping for ankle boots, stylist Kim Appelt recommends considering your lifestyle, body type and location.
If you live in a colder climate, choose ankle boots made from leather, suede or shearling. But if you live in a warmer city, opt for boots that can transition well through seasons, such as boots made from faux leather, polyester and synthetic materials. These materials won't provide intense insulation and have better resistance in mild weather conditions.
"Look for premium calf, nappa leather or suede for that classic look and feel — they offer durability, breathability and will only get better with wear," adds the president of Donald Pliner, Ginnie Bond.
Also, stylist Sandra Okerulu recommends ankle boots that are no more than 2 inches high because they can be worn as everyday shoes. (Plus, they can resist a long day of work.)
"You want to buy boots that have a 2-inch heel, give you lift and leverage your style for work and the evening," adds Okerulu. For more style tips and how to find the perfect fit, scroll to the FAQ section.
Expert-approved ankle boots
"For my minimalist girlies who love an edge, mini slouch booties are the win for this season. The slouch can convert into your everyday life and add another look to your outfits. This is a trend that you will be seeing in the streets and runways," shares Okerulu. Additionally, this pair combines the edge of a Western style as well.
"The Western boot is also holding strong, but this season it’s a cleaner, city-ready version. No heavy embroidery — just sleek lines that slip easily into wide-leg trousers or denim," says Appelt. This pair offers the comfort of a kitten heel with the aesthetic of a Western design. According to a shopper, this pair fits true to size and is super comfortable to wear.
I love leather, and both stylists agree that this is a must-have material for the fall season. These ankle boots have a sturdy lug sole and the perfect height to wear with wide-leg denim and dresses. Plus, leather can be worn with casual and elegant pieces simultaneously, all year-round.
"Slouchy suede ankle boots are big this fall. Think rich burgundies and chestnuts with that effortless, scrunched-down vibe. They’re relaxed but chic, perfect for giving jeans or dresses a little boho polish," says Appelt. Many shoppers have given this style their thumbs up for its cozy interior, versatile design and overall comfort.
"For those who like to make a statement, animal-printed ankle boots are everywhere — snakeskin, leopard, zebra. Paired with square toes, it’s a bold but wearable nod to both the ’80s and ’90s," shares Appelt. This style features a size zipper for easy wear and an almond toe box that will give your toes some room to move around.
"The sock boot is officially back. Streamlined, form-fitting and surprisingly versatile — it’s that quiet, minimalist cool that works for day or night!" shares Appelt. This one features memory foam and a block heel for everyday commuting. The ribbed knit upper hugs the ankles, and it adds an effortless vibe to any look.
Okerulu chose this pair for its elegant silhouette that can transition from day to night. LifeStride shoes are known for their comfort technology and feminine designs. This is evident in the footbed construction, which is made with the brand's Soft System, and is packaged with extra cushion and flex to allow all-day comfort.
"These Dolce Vita Stef Booties are not only calling for a stylish moment, they offer a cowgirl aesthetic as well," says Okerulu. The Western trend is still going strong and there are many outfit variations you can create with this design. "The color pattern offers versatility, whether you dress them up or down," says Okerulu.
Whether you love to keep it edgy or add some balance to your outfits, Appelt recommends boots with a chunky tread. Additionally, if you have an inverted triangle body type, this will help draw attention to your lower half. Opt for boots with details or buckles like this one to add some proportion to your bottoms.
I [Espinal] own this pair, and it is a nice addition to my fall casual fits. The pair is spacious enough to wear thicker socks with and features a comfortable molded footbed for days that might require standing for longer hours.
Best ankle boots, approved by editors
I've [Espinal] worn my pair of Minnetonka shoes for the past decade, and it's been one of the best pairs of ankle boots I've bought during a trip to Atlanta, Georgia. This is another iteration, and it's similar to the one I currently own. These are easy to wear and can be worn with thick socks — ideal if you want extra warmth as well. Plus, they're ultra comfortable. Additionally, they feature a rubber outsole that provides excellent grip to help protect you from slips and falls.
While combat boots are slightly slowing down this season, I still appreciate the classic design from Timberlands. This style has been on my wish list for the longest due to its overall comfort, warmth and sturdy outsole. This is a statement boot that translates well into many seasons while keeping your feet comfy even during the longest commute.
For rainy days, these ankle boots are a must-have. I own a pair of Vivaia flats, and I'm confident the ankle boots are as comfortable as they are. They feature arch support, a cushioned interior and a low heel for easy walks. The pair comes in multiple colors and sizes to upgrade your close-toe footwear collection, but the real standout feature is the water-resistant fabric that will hide any water evidence.
I own a similar pair from Dingo 1969 that features embroidered details. However, to keep things classier, I would opt for a Western design that features more minimalist adornments, as advised by Appelt. The brand offers its signature cushioned interior with sturdy rubber outsole to keep you comfortable all day.
Deputy managing editor Jess Bender has jumped onto the sock trend with this comfortable pair from Everlane. "Stylish, supportive, capable of withstanding several types of terrain — this bootie checks all of the boxes for me," says Bender.
While it has a higher price tag, Bender caved in after several members of a podcast community raved about them. "I was enamored from the moment I slipped these on. Much like their title promises, these really do feel like a glove would for my feet. The height gives me a bit of extra height, but not too much where it feels like I'm walking on stilts. Most importantly, I've worn these in various settings over the last several months — from pacing around the halls in the office to dates around my neighborhood to exploring the nightlife around Portland — and my feet barely felt the mileage I walked around in them," she explains.
Associate editor Kamari Stewart has this pair in her fall footwear rotation because of its versatile design. "I had a pair of similar boots that I wore until they were literally falling apart and aren’t made anymore. When I saw these, I instantly fell in love because I knew I’d get a lot of use out of them. While some people are sad summer is ending, I’m excited about the cooler temps that fall brings so I can start to wear these soon!"
Frequently Asked Questions
Appelt recommends wearing a suede kitten heel or pointed boots with wide-leg jeans and a blazer. Most ankle boots pair very well with denim and a blouse. For the evening, Appelt recommends wearing a leopard dress or a black dress.
"For example, wearing a pencil skirt with ankle boots is tricky. You need to know how to style the top and play with proportions," says Appelt. If it gets colder, you can add tights since ankle boots transition well into the evening.
Bond also suggests adding a "relaxed sweater or layer on a casual jacket for a cool and casual weekend-ready look, perfect for tailgating or pumpkin patch picking. Suede boots in rich earthy tones complement that casual chic style, giving your outfit both cozy comfort and a touch of warm, modern femininity."
As for the evening, Bond advises opting for sleek leather or sculpted heel shapes to elevate your look. "Pair with tailored dress pants or a statement skirt to create a refined, fashion-forward outfit. For a fancy night out or an alternate twist on wedding guest attire, consider pairing pointed-toe boots with a long, flowing dress — a striking, fresh contrast we adore," says Bond.
Okerulu, Bond and Appelt recommend sizing up when it comes to ankle boots because the socks can add extra inches of thickness to the fit. "For the most part, you want to go up one size and shop for shoes at the end of the day when your feet are swollen. This will help you identify the right size," says Appelt.
"Leather takes a while to stretch and you want to size up when you buy this kind of material," says Okerulu.
"A good ankle boot should offer enough room in the toe box without feeling too tight, allowing you to wear them all day with ease," adds Bond.
Appelt says the ankle boots trending for fall 2025 include slouchy suede boots, Western styles, animal-printed boots and the sock boot.
"Ankle boots are incredibly versatile and can be worn with a variety of bottoms. They pair perfectly with jeans, straight-leg trousers, or even wide-leg pants, as long as the hem hits just above the boot," says Bond.
You can also wear ankle boots with a midi skirt or dress to balance out the silhouette.
Bond adds a pro tip: "To maintain the timeless elegance of your leather boots, we recommend cleaning them after every few wears, especially if they've encountered dirt, rain or grime. With continued use, the leather will mold to the shape of your legs and quickly become your favorite boots. Regular maintenance is key to preserving their luxurious finish and extending their lifespan."
How we chose
We asked stylists for their recommendations on ankle boots and which styles are trending for the fall 2025 season. Shop TODAY editors also tried their favorite picks while considering availability and size inclusivity.
Meet the experts
- Sandra Okerulu is is an accomplished celebrity style expert who has styled some of the biggest names across the world.
- Kim Appelt is a personal and celebrity stylist and author of the Amazon bestselling book “Style for Everybody,” which focuses on creating a classic and timeless wardrobe for individuals based on their body, style and life.
- Ginnie Bond is the president of Donald Pliner, a footwear luxury brand focused on men and women.
