As the weather begins to cool down this time of year, I start digging my all-time favorite accessories out of hiding: Boots. The best boots are fashionable and versatile and can pair with almost anything, from a denim outfit to a slinky slip dress—but of all the boots out there, ankle boots often reign supreme. Fashion stylist Sarah Nearis agrees, calling ankle boots her "personal favorite"; she describes them as "ankle boots or booties that cover the whole foot and reach up to or a little past the ankle." Because of their height, ankle boots are also great in the early fall, when temperatures are just beginning to drop, but don't quite warrant snow boots.
"As sad as I am to admit fall is right around the corner, I love the fashion that comes with it and the weather that allows for more boots," Nearis says, advocating particularly for ankle boots because of their ability to remain a steadfast everyday shoe, noting, "Ankle boots are so versatile depending on the style and design. There are so many ways to style them."
Below, we've gathered some of our all-time favorite ankle boots for fall and winter so that when you invest in your new favorite style, you know you're getting the very best.
- Best Everyday Ankle Boots: Rothy's The Lug Boot
- Best Heeled Ankle Boots: Christian Louboutin Black Suprabooty Boots
- Best Cold Weather Ankle Boots: Naot Pali Faux Shearling Lined Bootie
- Best Transitional Ankle Boots: Madewell The Hempstead Desert Boot
- Casual Ankle Boots: Minnetonka Back Zip Hardsole Bootie
- Best Ankle Boots Overall: Saint Laurent West Chelsea Boots in Smooth Leather
"I'm obsessed with how Rothy's manages to rejig traditional styles into comfy, minimalist hero shoes—the kind you'll reach for every time you walk out the door, whether you're walking the dog or going out for a fancy dinner," says digital director Jenny Hollander. "For spring and summer, I love their flats, but for fall and winter, I'm a big fan of their ankle boots. They're far more comfortable than a regular ankle boot, and will last you season after season."
"For an everyday boot, I love BYFAR ankle boots," Nearis recommends. "The heel is more of a block heel and they come in such great colors―they have a bit of a 60’s vibe." This taupe pair certainly makes a retro fashion statement, featuring a high yet comfortable block heel that’s built for stability. According to the brand, their shoes also fit true to size, though bear in mind that they utilize European sizing.
Nearis says that this is one of her all-time favorites, calling the luxe boots, "timeless and a great investment pair." Indeed, they’re made from 100 percent calfskin leather for a buttery soft feel that’s made to last. The grooved heel, measuring at about two inches, is also built for comfort and stability, and the back tabs and elasticized sides (reminiscent of a Chelsea boot or Cuban heel) make the pair easy to pull on and slip off. It’s a pair you’re bound to wear for a lifetime.
"Everyone needs a pair of simple black ankle boots in their closet, and this Sam Edelman pair is mine," gushes Marie Claire Contributing Writer Brooke Knappenberger about this structured, square-toed pair, which is made from 100 percent leather and features a three inch heel. "These quickly become my most-worn shoes in the fall since their super sleek style goes with almost everything I own. Plus, the low heel makes them comfy enough to wear to work!"
These boots include both a playful (but not too high) heel and a fun color, making them an easy accessory to opt for when you need to spice up a plain outfit. They're also highly rated online, with one customer calling them their "new favorites." Made from Brazilian leather that promises to be both durable and comfortable, their two inch heel makes them perfect for running to work or for a night out. They fit true to size, but are on the snug side, so size up if you have wider feet or prefer thick socks.
These ankle boots from Naot feature a classic style and silhouette that’s perfect for both fall and winter, and their faux shearling upper and lining serves as both a style boost and a bit of added warmth. Made from soft leather that molds to the wearer’s foot, they’re guaranteed to be an autumn go-to, especially since they have a cushioned (and removable!) insert designed to provide extra arch support.
If you're looking for a pair of heeled boots that's still suited for comfortable walking, consider this pair by Sorel. Reviewers love the "chunky, stable" four-inch heel, and say that they're durable with a soft interior. They’re also made from fully waterproof leather, which comes in handy during the unpredictable weather of the fall months. And when it comes to safety, never fear—they feature a rubber sole that resists slippage, even on the slickest floors and city streets.
For a more elevated look and luxury experience, consider these boots from Christian Louboutin. Their pointed toe and signature red leather sole are bound to turn heads. And if you’re concerned that they’re all form with no function, guess again: Made from calfskin leather, they have a rubber and leather sole as well as a rubber injection at the heel. Plus, their zip closure is on the inner side so that the silhouette remains smooth, the soft leather uninterrupted.
These boots have the structured look of Oxfords, leaning into the classic, Dark Academia look that’s all the rage this fall. Plus, they have a lug sole, meaning that their rubber sole includes deep indentations that make for better, more stable footing when you’re walking to walk or traipsing around town. They’re also padded on the inside so you can feel comfortable standing in them for hours on end, and they even come in half sizes, so you can be sure you’ll find your perfect fit.
Do you miss the days of bedazzling everything in sight? Look no further than this pair of luxury boots from Kendall Miles, which elevates the glittering look of gemstone accessorizing so that it works for your grown-up needs. The leather pair comes in both black and white, and features constellations of glass gems outlined in gold. The heel, too, is covered in leather and gemstones, and the leather insole is double padded for optimal comfort and durability.
These boots bring the best of both modernity and classic Western style, with their pointed toes, traditional silhouette, and studded soles. Opt for them in tan for a timeless traditional look, or choose from one of the 10 additional colorways, like deep red, light pink, washed black, or light blue. In addition to being striking, according to reviewers, these shoes are also unbelievably comfortable. Onne customer writes, "I have neuropathy and bunions, and these boots are a dream for my feet."
I'm obsessed with these boots. Although I usually opt for a pair of boots with a heel, these are unbelievably comfortable, and they look chic to boot (pun intended). I especially love wearing them when I'm travelling or when I know I'll be having a hectic day. They’re also warm and spacious enough to wear with thick socks—a quality I appreciate as temperatures drop or when inclement weather (i.e. snow) begins to rear its frigid head.
This is another pair I love and positively live in when I need a break from my heels. These boots have a firm hardsole designed to handle city streets, yet they're so comfortable that they feel like house slippers. They feature a suede lining and upper, making them the perfect go-to pair for the fall. I also love the Bohemian look of the fringe around the angles, which looks fabulous with a pair of jeans or even with a short denim skirt and tights.
Yes, boots can have cutouts, too. This style is especially popular in autumn, when temperatures can hover around the 60s and 70s, making warmer, fur-lined options a little too sweat-inducing for most wearers’ tastes. This option from Ganni is among my favorites, with its bulky hardware that lends the shoe a tougher, more punk-inspired look. The buckles are also adjustable, making these boots ideal for the wearer that’s between sizes. Made from animal-friendly faux leather and a 100 percent rubber sole, they’re sure to make a statement all season long.
Meet the Expert
Sarah Nearis is a fashion stylist and creative director. She is based in Los Angeles and Nashville.
