Asos Design Remmy Set Back Heeled Boots
Have you ever wondered how to wear ankle boots with straight leg jeans? The key is to contrast the looser fit of the denim with heeled ankle boots. That’s why we like this design from ASOS. The pointed toe and set back heel gives jeans a sharp, sophisticated look when worn together. The design and authentic-looking faux leather will fool even the most stylish onlooker that these are a designer pair.
Nine West Donda Heeled Booties
Add just the right amount of edge to your outfit by wearing these studded ankle boots with a dress. Made with real leather, these booties are designed to last. The flattering rounded toe, smooth leather, and rich shades ground the boot in elegance while the studs add some attitude, so they are easy to dress up or down.
Free People We The Free Wesley Ankle Boots $298
In America, youre free to embrace any footwear trend you choose, but we recommend the western one. These brown leather boots from Free People have just the right amount of cowboy flair while remaining simple enough to dress up or down with any fall outfit. Best yet, they come in nine different colors from browns and black to fun shades like red, blue and white.
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Louise Et Cie Jadran Pointed Toe Bootie
Trying to match ankle boots with a dress that leans more towards the formal side? These elegant booties from Louise Et Cie are perfect. The unique combination of suede and smooth leather makes these more than just another pair of black booties. A pointed toe and sculptural heel give the boots a sophistication that could easily go with a midi skirt or a dress that hits above the ankle. Whether you’re dressing up for a fancy dinner or an important presentation at work, these boots will have you striding with confidence.
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These boots are made for walking and jumping into fall leaves, strolling through apple orchards and kicking back around the bonfire.
Fall boots and booties are a wardrobe staple, and with so many colors and styles to choose from, they quite possibly take up quite a chunk of that wardrobe when October rolls around.
After cleaning out your shoe closet and retiring those that have worn out soles and scuffs, take inventory to see which trending style you need to stock up on.
Western and cowboy booties were super in for Fall 2021, so weve included them again as a separate category down below.
For now and every time of year, make sure to check out Chelsea boots in every color in both leather and suede. Then grab a pair of peep-toe booties for date night when you want to show a bit of skin.
From Kenneth Cole and Hunter Boots to Coach, UGG and more, take a look below for the best fall booties for every style and budget.
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Kat Maconie Alba Chain Heel Boot $369
We already told you that gold chains were in, but we never knew they could be incorporated into a black fall bootie. From Kat Maconie, this black ankle boot looks innocent enough from the front, but turn to the side to find an incredible circular chain-link heel, measuring 7.5cm or just under three inches.
Steve Madden Hutch Black Bootie
We love lug-soled boots not only because they are the “it” boot of the season, but also because they are surprisingly practical. The thick treads make walking in the snow a little bit easier and the chunky sole gives you height without pain. With its tomboy toughness, a lug-soled ankle boot like this one from Steve Madden looks amazing when contrasted with a more feminine dress or skirt. Choose between black and beige.
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How To Wear Ankle Boots With A Dress Or Skirt
Ankle boots can also look incredibly stylish when worn with a dress or a skirt, no matter the length. Whether you’re rocking a maxi skirt on the weekend or sporting a midi dress to work, there is an ankle boot that will work with your outfit.
This neutral sweater dress and versatile black boots make for a great style combination. Play with texture by mixing a jewel-tone velvet skirt with studded booties and a bucket bag. A chic high-low turtleneck streamlines the look. A maxi dress can also have a major impact with the right bootie peeping out from beneath the fabric. Consider a black zip-up bootie, like the one pictured above, for a sleek, cool-girl vibe.
Flaunt A Bolder Style In Women’s Ankle Boots
Add a pair of versatile women’s ankle boots to your wardrobe and give your work, date, or casual outfit an edge. Enjoy ankle shoes that are as comfortable as they are stylish, with features such as an easy slip-on design, cushioned footbed, and outsole traction.
Ankle boots with a square or round toe box let toes spread out and avoid the pinching sensation common in shoes with narrow toes. Flat ankle boots with arch support keep feet properly aligned to minimize discomfort and injury. Experience cushioning and stability in ankle boots with a padded insole. While all heel boots can boost your height and enhance your posture, wedge or stacked heels provide a comfortable, wobble-free stride. Slip your feet in easily, and keep them in place in ankle boots with side zippers, laces, or elastic goring. Accentuate your look for any setting or event with boots in the right color and material. Complete your work outfit with leather boots for a polished look, or match a flowy skirt with a suede Chelsea boot for a music festival.
Take advantage of free shipping and 365-day returns when you order women’s rain boots and other footwear from Zappos. For questions about our products and services, call our 24-hour customer support. Search our shoe collection for the latest booties, knee-high boots, and ankle boots to keep your style updated.
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How To Wear Ankle Boots With Dress Pants Or Cropped Pants
Ankle boots look just as great with dress pants and cropped trousers as they do with denim, so step outside of your comfort zone and give the style a whirl. Patterned boots and chunky jewelry add a bit of edge to paper bag-waist pants and a slouchy, off-the-shoulder pullover. Cropped flares ensure that your ankle boots stand out, while a slight heel gives you a little boost .
The color palette in this outfit feels appropriate to fall moody hues like beige and black are a great neutral combination for the season. Try tucking your pants into ankle boots for an ultra-stylish look that works just as well at work as it does on the weekend.
Steve Madden Lynden Block Heel Bootie
For a fun pop of color, these patent heeled booties won’t disappoint. Choose from bold hues like pink, blue, and white or stick to the basics of black and brown. With a 4-inch heel, these ’60s-inspired booties look best when paired with modern pieces like jeans. That way, it won’t seem like you are wearing a costume, and they will add a funky retro vibe to your outfit. Best of all, the patent material is easy to cleanjust wipe with a damp cloth, and you should be good to go.
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Womens Ankle Boots All Year
Short boots arent just for winter anymore! With a peep toe or open heel, they become the perfect transitional style. As the snow melts, break out a Western-inspired cutout boot. For warm weather, show off that pedicure with an open toe summer bootie. In fall, opt instead for ankle boot with playful perforation or just a hint of faux fur.
How To Wear Ankle Boots With Jeans

Wearing ankle boots with jeans is a great way to ease into the bootie trend if you’re just not sure what to pair them with. Whether you are dressing your jeans up or down, there are different types of ankle boots you can wear to stylishly assist in the process.
Cropped jeans and ankle boots are a match made in heaven. Cuff the hemsinstead of tucking them into the bootsfor some major ankle action. The cropped hemline creates a frame for showing off your favorite booties. If you’re going for a really casual look, wear brown ankle boots with cuffed jeans for a relaxed vibe. If you want to add an extra element of style to your denim outfit, make sure your booties have a pop of color. Finally, pair the look with an oversized sweater for a casual fall ensemble that still looks polished.
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Best Overall Ankle Boots
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The 14 Best Ankle Boots For Women In 2022
The essential fall shoe.
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 dressbut 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.
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House Of Harlow X Revolve Nick Bo
The beauty of snakeskin booties? They practically are neutral thanks to the blend of black and brown shades and thus go with nearly every outfit. This style’s cool pattern and pointed toe deserve to be shown off, so a cropped pair of pants will do them justice. Feel free to coordinate your top with the neutral shades or simply pair them with a bright color for a funky look.
Hunter Womens Original Chelsea Boots $150
Dont let anything rain on your fashion parade this fall. If you need a rain bootie, turn to the experts at Hunter Boots and check out the cropped version of their original rain boots. The Chelsea style is very on-trend and easy to wear, and of course they also feature the Hunter logo and pull tabs at the back.
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Sam Edelman Garret Combat Platform Boot $180
Take black classic combat boots and flip them on their head. These all-white combat boots from Sam Edelman really make a statement, as even the laces and hardware are white for a sleek look. If you dont love the ivory, they also come in an array of brown and black leather, but these are truly the standout shade.
Best Heeled Ankle Boots
“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 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.”
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 fallthey fit in perfectly with the autumnal foliage and orange-tinted decor.
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