“We call a bootie a shoe or low boot that extends just below or above the ankle bone,” says Rigamonti. “There are many variations of a bootie as they can be flat, have a heel, a wedge, or a platform.”

Are ankle boots still in style?

Rigamonti says she doesn’t believe that ankle boots will ever go out of style because of how universally flattering they seem to be. “Ankle boots can be worn in dozens of unexpectedly stylish ways for almost any occasion in any season,” she points out. “They look great when paired with dresses, skirts, shorts, trousers, and jeans.”

How do you wear ankle boots with jeans?

First of all, whether you wear them with a skirt or a pair of pants, you should show a bit of leg. With jeans specifically, all you have to do is leave some naked space between your jeans and the boots,” Rigamonti explains. "You can achieve this by either cuffing the jean or finding a denim length that hits above the ankle and pairing it with a boot that has the right proportions.”

12 Best Booties for Women in 2023

What is a wardrobe without a pair of trusted ankle booties? The shoe style is an indispensable wardrobe staple that can not only transition you into fall and spring, but also pull your looks together in the thick of winter as you navigate heavy winds, rain, salt, and snow.

Of course, not all booties are made the same. In finding the best pairs to shop for, we considered shape, heel height, versatility, and waterproofness. We also spoke to Aerosoles’ head of design Fabiana Rigamonti for even more insight on what makes a great pair.

Byrdie Researched & Approved

Our top pick is Dr. Martens 2976 Chelsea Boot, the brand’s original Chelsea style and a perfect solution for those looking for a more subtle take on Docs. Those looking for a slimmer shape and a block heel for well under $100 should take a closer look at Old Navy's Faux-Suede Western Ankle Boot.

Our Top Picks

Best Overall:

Dr. Martens Chelsea Boots at Amazon

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Best Budget:

Old Navy Western Ankle Boots at Gap.com

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Best Designer:

Brother Vellies Platform Boot at Nordstrom

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Best on Amazon:

Amazon Essentials Ankle Boot at Amazon

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Best Cowboy :

Schutz Leather Bootie at Schutz-shoes.com

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Best Square-Toe:

By Far 14 CM Boot at Byfar.com

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Best Kitten Heel:

STAUD Ankle Boot at Staud.clothing

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Best Chelsea :

Sam Edelman Laguna Waterproof Lug Sole Chelsea Boot at Nordstrom

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Best Lug Sole:

Palladium Revolt Boot at Palladiumboots.com

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Best Waterproof:

UGG Drizlita Boots at Ugg.com

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In This Article

Our Picks
What to Look for
FAQ
Why Trust Byrdie

Dr. Martens

View On Amazon View On Nordstrom View On Walmart

If you could only pick one pair of ankle boots as an investment, it should be the 2976s. They're the brand’s original Chelsea style and serve as a perfect solution for those looking for a more subtle take on Docs. The low heel works well with casual and dressy looks alike, while the leather upper and thick rubber sole will help you to navigate wet, winter weather with ease.

Price at time of publish: $170

Materials: Leather | Size Range: 5–12

Old Navy

View On Gap.com

In classic fashion, Old Navy makes a pair of under-$40 ankle booties that are perfect for everyday wear with wide-leg or skinny jeans. (The shaft appears too wide to suit a straight-leg silhouette, but you can be sure of this upon trying them on.) In terms of height, the block heel is a manageable 2.25 inches high and offers more stability than a slimmer one.

Price at time of publish: $40

Materials: Recycled thermoplastic rubber, thermoplastic rubber | Size Range: 6–11

Nordstrom

View On Nordstrom

Channel the ’70s in Brother Vellies’ Empire Platform Boot. The style features a chunky, 1.5-inch platform and a flexible, form-fitting shaft for a super sleek appearance.

Price at time of publish: $725

Materials: Leather | Size Range: 5–11

Amazon

View On Amazon

These low-cut ankle booties from Amazon come at a fantastic price point. Available in both faux suede and vegan leather in a range of neutral hues, they’re comfortable and easy to wear with everyday jeans as well as skirts and dresses. They even come in wide sizing to suit even more shoppers.

Price at time of publish: $22–$46

Materials: Faux suede, faux leather | Size Range: 5–15, plus wide sizing

Schutz

View On Schutz-shoes.com

Get in on the Western boot trend with these cowboy ankle booties from Schutz. They’re made from buttery leather that’s been embroidered with a fancy, albeit monochromatic, motif. Like any pair of classic cowboy boots, the low heel makes these practical for days spent on your feet.

Price at time of publish: $109

Materials: Leather | Size Range: 5–11

View On Byfar.com

Blunt-front footwear is on the rise, too. Case in point: these mod ankle boots from By Far x Mimi Cuttrell. They feature a form-fitting ankle shaft and a side zipper so you can slip in and out of them with ease. The platform booties seem to be a modern take on the go-go boot style and would pair well with flared jeans or a midi skirt.

Price at time of publish: $665

Materials: Leather | Size Range: EU 35–41

STAUD

View On Staud.clothing

In terms of footwear, there are few things more practical than a kitten heel. That said, STAUD’s Wally Ankle Boot offers the right amount of lift. And thanks to its minimalist design, the style rounds out so many outfits, from jeans-and-T-shirt looks to frilly midi dresses.

Price at time of publish: $395

Materials: Suede, leather | Size Range: EU 35–42

sam-edelman-laguna-waterproof-lug-sole-chelsea-boot

Nordstrom

View On Nordstrom View On Macy's View On Samedelman.com

These Chelsea boots from Sam Edelman come in either leather or suede and eight neutral hues, including bright white, tan, and black. With a 1.5-inch heel and platform lug sole, the style offers a utilitarian sensibility, too. However, you can rest assured that the most classic and beloved Chelsea boot elements, such as the elastic gussets and the pull tabs, have not been forsaken.

Price at time of publish: $99–$170

Materials: Leather | Size Range: 5–14

Palladium

View On Palladiumboots.com

Palladium shoes are made with durability in mind, many thanks to the signature lug soles on many of the brand’s styles. This boot in particular was inspired by the combat aesthetic and features a super chunky, serrated platform sole and lace-up design. Though what’s just as nice is how easy to slip on and off they are with a zipper on the inside of the ankle shaft.

Price at time of publish: $150

Materials: Leather | Size Range: 5–11

UGG

View On Ugg.com

UGG’s Drizlita booties are so good at keeping your feet warm and dry, reviewers say. Their low shaft height also makes them easy to take off and temporarily stow, should you want to wear these on a commute and change into a pair of heels upon arriving at the office.

Price at time of publish: $90

Materials: Synthetic | Size Range: 5–12

Dear Frances

View On Dearfrances.com

Make a statement in these architectural, block heel booties from Dear Frances. They’re made of buttery soft leather but sit on shiny, patent leather heels. Pick from a mix of finishes including tan, black, brown snakeskin, and Barbiecore pink to elevate virtually any winter ’fit.

Price at time of publish: $610

Materials: Leather | Size Range: EU 35–42

Dr. Martens

View On Drmartens.com

We have a lot of love for these Heart Leather Platform Boots from Dr. Martens, and it’s not just because of the sweet, heart-shaped buckles. If anything, there’s something to be said about contrast, like the tough, rubber platform sole on the shoe style and signature, ungendered yellow stitching. Wear them with everything from straight-leg jeans to miniskirts, mini dresses, and tailored shorts

Price at time of publish: $180

Materials: Leather | Size Range: 5–11

Meet the Expert

Fabiana Rigamonti is the head of design at Aerosoles.

What to Look for in Booties

Fit

“You should note the shaft height of the boot and how tight they fit around the ankle,” says Rigamonti. “Boots that dig into your ankle or cut into a part of your leg will not be comfortable.” In addition to comfort, she says the fit is also important for styling. “Slimmer and higher shafts tend to pair better with dresses, skirts, and leggings, while lower shaft booties—like a classic Chelsea—go best with jeans, especially when you style them to show a little ankle,” she explains.

Heel Height and Toe Shape

You also want to consider the various design elements of a bootie, like the heel height and the toe shape, and how they might work together. “Heeled booties with a pointed or rounded toe tend to elongate the leg and be a flattering fit for almost anyone,” Rigamonti says.

FAQ

What is a bootie?

“We call a bootie a shoe or low boot that extends just below or above the ankle bone,” says Rigamonti. “There are many variations of a bootie as they can be flat, have a heel, a wedge, or a platform.”
Are ankle boots still in style?

Rigamonti says she doesn’t believe that ankle boots will ever go out of style because of how universally flattering they seem to be. “Ankle boots can be worn in dozens of unexpectedly stylish ways for almost any occasion in any season,” she points out. “They look great when paired with dresses, skirts, shorts, trousers, and jeans.”
How do you wear ankle boots with jeans?

First of all, whether you wear them with a skirt or a pair of pants, you should show a bit of leg. With jeans specifically, all you have to do is leave some naked space between your jeans and the boots,” Rigamonti explains. "You can achieve this by either cuffing the jean or finding a denim length that hits above the ankle and pairing it with a boot that has the right proportions.”

Why Trust Byrdie

Contributing writer Jessie Quinn has a Bachelor’s Degree in Fashion Journalism from Academy of Art University. At Byrdie, Jessie covers everything from accessories to denim trends. Next to sneakers, boots are Jessie’s most-worn and most-loved shoe style, and she’s particularly fond of the timeless ankle bootie. In researching the best booties for women, she took into account the various shapes, fabrications, and thoughtful details added by designers to make a given pair unique.

The 12 Best Chelsea Boots of 2023