As the weather begins to cool down this time of year, I begin digging my all-time favorite accessories out of hiding: Boots. The best boots are fashionable, versatile, and can be paired with just about any outfit, from a denim outfit to a slinky slip dress—but of all the types of 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 bootie 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 Heeled Ankle Boots
"For an everyday boot, I love BYFAR ankle boots," Nearis recommends, continuing, "The heel is more of a block heel and they come in such great colors―they have a bit of a 60’s vibe."
Nearis names this pair as another of her all-time favorites, calling the boots, "timeless and a great investment pair."
"Everyone needs a pair of simple black ankle boots in their closet, and this Sam Edelman pair is mine," gushes Marie Claire Editorial Fellow Brooke Knappenberger. "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."
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" heel, and say that they're durable with a soft interior.
These booties are chic and perfect for those transitional days between summer and fall. They also have a perfect online rating, with one customer saying that they're so comfortable, they don't even feel like high heels.
Frye is one of my favorite boots brands, and this pair is a great example of why. This redwood colorway is a sleek, classic look that's upgraded by the original braided detailing along the side. I tend to wear this pair in late fall―they fit in perfectly with the autumnal foliage and orange-tinted decor.
Best Low-Heeled Ankle Boots
"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 Jenny Hollander, Director of Content Strategy. "For spring and summer, I love their flats, but for fall and winter, I'm a big fan of their Merino ankle boots. They're far more comfortable than a regular ankle boot, and will last you season after season."
Interested in a fun-yet-grown-up version of bedazzling? Look no further. While many style of boots use a buckle to add some shine to their style, I love the way this pair from Kendall Miles incorporates shiny little jewels to create a star-like effect.
These combat ankle boots include a knitted upper level for a snug, comfortable fit (which I personally appreciate―especially when they're worn under a pair of jeans). They come in four colorways, but I personally love this subtle khaki shade.
These boots provide a means of incorporating both modernity and classic country-Western style into your wardrobe, but they're also great beyond that: According to reviews, they're unbelievable comfortable, with one customer writing, "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 love wearing them when I'm travelling or when I know I'll be having an especially hectic day.
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.
Just because it's raining, doesn't mean you need to forego style. These Chelsea boots have a gloss to them that rivals even the finest patent leather, and review after review cites them as "perfect" rain boots.
Meet the Expert
Sarah Nearis is a fashion stylist and creative director. She is based in Los Angeles and Nashville.
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