Ankle boots are a timeless classic that has been around for ages, but the modern ankle boot of today has been updated to meet contemporary demands.

Free People is embracing the trend and has created its line of fashion-forward ankle boots that bring style and comfort together. Whether you’re looking for something casual for everyday wear or something a bit more sophisticated for a night out, Free People has something that will fit your style perfectly.

From boho-chic to western vibes, these designs are sure to give you the look you’re after while keeping you comfortable all day long.

Free People Charm Double V Ankle Boot

  • The Free People Charm Double V Ankle Boot features a pull-on style and ankle-height design with V-shaped cutouts at both sides, bold block heels, and eye-catching pointed toes. The perfect touch to your chilly weather ensemble.
  • Slip on style in an almond toe silhouette.
  • Cushioned insole provides all-day comfort.
  • Low profile stacked heel.
  • Leather upper, lining, insole and outsole.
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The first pair of ankle boots from Free People is the Charm Double V Ankle Boot. This bootie is made from premium leather and features a low stacked heel for added comfort, making them the perfect option for all-day wear.

The sleek design of this ankle boot makes it ideal for everyday looks – simply pair it with a dress or jeans and a blouse to create the perfect ensemble.

Free People Back Loop Ankle Boot

  • The cold-weather is calling your name in the Free People™ Back Loop Ankle Boot.
  • Pull tab on back.
  • Buckle strap for secure fit and comfort.
  • Slightly lifted heel with cushioned footbed.
  • Slip on style with pointed toe.
  • Leather upper.
  • Leather and textile lining and insole.
  • Durable synthetic outsole.
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The Back Loop Ankle Boot is another great option from Free People.

This boot features a unique buckle strap design that gives it an edgy and modern feel.

The heel is slightly elevated to provide comfort without compromising on style, making these ankle boots perfect for both work day and night occasions.

Plus, the back of the boot is slip on to making them easy to wear.

Free People Atlas Chelsea Boots for Women

  • Bring in the winter season with the ruggedly chic details of the Free People Atlas Chelsea Boot.
  • Chelsea boots feature a mixed leather upper with scalloped detailing and stud accents.
  • Pull-on wear with dual elastic gore side panels.
  • Leather and textile lining.
  • Lightly-padded, fixed footbed.
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If you’re looking for something a bit more casual, then the Atlas Chelsea  Ankle Boot is a perfect choice.

Crafted from luxe mixed leather, this boot features an almond toe that gives it a classic look while still remaining modern and stylish.

The wedge heel provides a little extra comfort and stability, making these boots ideal for everyday wear.

Plus, the boot is an effortless boho look that will pair perfectly with your favorite denim skirt.

Free People James Chelsea Boot

  • Gear up for the cooler weather with the leather Free People® James Chelsea Boot featuring a pull-on design with dual goring and side zip closure for a comfortable, yet secure fit.
  • Soft leather lining and cushioned leather-covered footbed for added comfort.
  • Durable heel and lugged synthetic outsole.
  • Made in Spain.
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The James Chelsea Boot is a great choice if you’re looking to add a bit of dramatic flair to your ensemble.

These boots feature a rubber sole  that give them a fun, laid back look without compromising on style.

The rubber heel provides comfort while still keeping you trendy, making these the perfect ankle boots for a day of shopping or running errands.

Free People Essential Chelsea Boot

  • These gorgeous Free People™ stacked heel booties from Spain are a must have!
  • Leather upper.
  • Zipper back closure.
  • Closed-toe silhouette.
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The Free People Essential Chelsea Boot is just that - essential. With a classic silhouette, stacked heel and choice of four shades, the Essential will become your new everyday boot.

Style them with a ribbed dress and be prepared to turn heads.

Free People Animal Charm Double V Boot

  • Elevate your fashionable look wearing the Free People Animal Charm Double V Boot, featuring an ankle-height design with V-shaped cutouts on both sides, bold block heels, and eye-catching almond toes
  • FP Animal Charm Double V Boots are crafted with a smooth leather upper, a breathable leather lining and cushioned leather insole, and are set on a stacked heel with a textured leather outsole
  • These Free People ankle-length boots with deep V-shaped cutouts on the side showcase an easy pull-on construction, making them easy to wear while on-the-go
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The Free People Animal Charm Double V Boot is a head turner. Crafted with quality leather and sporting an all over animal print.

This boot is a must have addition to your shoe collection. Pair them with a monochrome outfit featuring faux leather!

Free People Cecile Ankle Boot

  • Take the Cecile Ankle Boot out on an adventure through the city.
  • Leather upper.
  • Back zip closure.
  • Leather lining.
  • Lightly cushioned footbed.
  • Wrapped heel.
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Free People Cecile Ankle Boot snake embossed boots will elevate any outfit. try wearing them with tucked into coated denim jeans, add a faux fur jacket and you'll be ready for wherever it is your going!

Free People Vance Double Tab Chelsea Boot

  • Elevate your style with the sleek Free People™ Vance Double Tab Chelsea Boot.
  • Pull-on style with front and back pull tabs for easy on/off and added detail.
  • Ankle-high Chelsea boot shaft.
  • Closed round toe with cushioned footbed.
  • Durable rugged traction outsole.
  • Genuine leather upper.
  • Leather lining and insole.
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Free People Vance Double Tab Chelsea Boot is one of those styles that will always be on trend. The lug sole gives you an edgy look and is super comfy.

Pair these babies with jeans and an alpaca sweater for great cool weather style.

Free People Billy Boot

  • Step out in the Western-style FP Billy Boot, featuring ankle booties with flattering wrap-around buckled straps, studded detailing all around uppers, a pointed toe silhouette, and Western-style stacked heels
  • GENUINE LEATHER: FP Billy Boots boast an all-leather construction with a smooth leather upper, a breathable leather lining and leather insole, and are set on a stacked heel with a textured leather outsole
  • ZIPPER CLOSURE: These Free People ankle-length boots with deep showcase a side zipper closure on the inside of the shaft as well as adjustable buckled straps around the ankle for a precise and secure fit
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Free People Billy Boot allows you to channel your inner cowgirl.  From the stud details, wrap around buckle to the pointed toe, these boots will have you ready for the dance floor.

These are perfect date night ankle boots.

Free People Lawless Fringe Western Boot

Head out in style and enjoy the party in comfort wearing Free People Lawless Fringe Western Boot. Leather upper. Leather lining. Fringe detailing on the shaft. Block heel. Pointed toe. Side zip closure. Leather sole.

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Free People Lawless Fringe Western Boot takes cowgirl to the boho cowgirl level. Look out dance floor as you'll be two stepping all night long.

Style these beauties with a great GNO outfit!

Free People has something for everyone when it comes to ankle boots. Whether you’re looking for something casual for everyday wear or something a bit more sophisticated for special occasions, their collection of fashion-forward designs will give you the perfect look with comfort in mind.

From classic leather styles to western-inspired fringe details, there is an ankle boot from Free People that will fit your style perfectly.

So go ahead and give them a try – your feet will thank you!

We only recommend products we love and think that you will too. We may receive a portion of sales purchased from this article that was written by our Frilly team

Happy shopping!!