Stretch Ankle Boots

By Brand

Naturalizer

By Color

Other Options

Rosalie Leather Ankle Boots
Rosalie Leather Ankle Boots

Pricing

$195.00 or 5 payments of $39.00

Note:

Free Shipping

♥ SAVE CHANGES
Naja Stretch Ankle Bootie with Memory Foam
More choices
Naja Stretch Ankle Bootie with Memory Foam

Pricing

$59.95 or 5 payments of $11.99

Rating

3.7 5.0 3

♥ SAVE CHANGES
Impo Naja Chain II Stretch Ankle Bootie with Memory Foam
Impo Naja Chain II Stretch Ankle Bootie with Memory Foam

Pricing

$64.95 or 5 payments of $12.99

Rating

5 5.0 1

♥ SAVE CHANGES
Impo Naja Sequin Stretch Ankle Bootie with Memory Foam
Impo Naja Sequin Stretch Ankle Bootie with Memory Foam

Pricing

$64.95 or 5 payments of $12.99

♥ SAVE CHANGES
Elicia Chain Stretch Ankle Bootie with Memory Foam
Elicia Chain Stretch Ankle Bootie with Memory Foam

Pricing

$64.95 or 5 payments of $12.99

♥ SAVE CHANGES
Orval Stretch Platform Boot with Memory Foam
Orval Stretch Platform Boot with Memory Foam

Pricing

$102.00 or 5 payments of $20.40

Note:

Free Shipping

♥ SAVE CHANGES
Ovidia Stretch Platform Boot with Memory Foam
Ovidia Stretch Platform Boot with Memory Foam

Pricing

$74.95 or 5 payments of $14.99

♥ SAVE CHANGES
Ovidia Bling Stretch Platform Boot with Memory Foam
Ovidia Bling Stretch Platform Boot with Memory Foam

Pricing

$79.95 or 5 payments of $15.99

Note:

Free Shipping

♥ SAVE CHANGES
Orval Wide Calf Stretch Platform Boot with Memory Foam
Orval Wide Calf Stretch Platform Boot with Memory Foam

Pricing

$102.00 or 5 payments of $20.40

Note:

Free Shipping

♥ SAVE CHANGES
Naturalizer Madalynn Gore Water-Repellant Ankle Bootie

Customer Pick
Naturalizer Madalynn Gore Water-Repellant Ankle Bootie

Pricing

$109.99 or 5 payments of $22.00

Rating

4.3 5.0 27

Note:

Free Shipping

♥ SAVE CHANGES
Noeva Stretch Knit Ankle Bootie with Memory Foam
Noeva Stretch Knit Ankle Bootie with Memory Foam

Pricing

$54.95 or 5 payments of $10.99

♥ SAVE CHANGES
Patrizia Boots Obelia
Patrizia Boots Obelia

Pricing

$99.95 or 5 payments of $19.99

Note:

Free Shipping

♥ SAVE CHANGES
"As Is" Naturalizer Madalynn Gore Water-Repellant Ankle Bootie
"As Is" Naturalizer Madalynn Gore Water-Repellant Ankle Bootie

Pricing

$48.99
Original price of ~~$109.99~~
or 5 payments of $9.80

Note:

Only 2 left

♥ SAVE CHANGES
Donald J. Pliner Abbie Faux Leather Ankle Bootie

Clearance
Donald J. Pliner Abbie Faux Leather Ankle Bootie

Pricing

$173.80
Original price of ~~$258.00~~
or 5 payments of $34.76

Rating

5 5.0 1

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Women's Tru Comfort Foam Chayse Bootie
Journee Collection Women's Tru Comfort Foam Chayse Bootie

Pricing

$109.99 or 5 payments of $22.00

Note:

Free Shipping

♥ SAVE CHANGES
Tashra II Hidden Platform Wedge Bootie with Memory Foam
Tashra II Hidden Platform Wedge Bootie with Memory Foam

Pricing

$64.95 or 5 payments of $12.99

♥ SAVE CHANGES
Naturalizer Sampson Bootie
Naturalizer Sampson Bootie

Pricing

$139.00 or 5 payments of $27.80

Note:

Free Shipping

♥ SAVE CHANGES
Naturalizer Genn-Swerve Bootie
Naturalizer Genn-Swerve Bootie

Pricing

$139.00 or 5 payments of $27.80

Note:

Free Shipping

♥ SAVE CHANGES
Vance Co. Men's Marshon Chelsea Boot
Vance Co. Men's Marshon Chelsea Boot

Pricing

$99.99 or 5 payments of $20.00

Note:

Free Shipping

♥ SAVE CHANGES
Thomas & Vine Men's Nash Wingtip Chelsea Boot
Thomas & Vine Men's Nash Wingtip Chelsea Boot

Pricing

$179.99 or 5 payments of $36.00

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Womens Tru Comfort Foam Riplee Bootie
new! Journee Collection Womens Tru Comfort Foam Riplee Bootie

Pricing

$109.99 or 5 payments of $22.00

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Womens Tru Comfort Foam Estee Bootie
Journee Collection Womens Tru Comfort Foam Estee Bootie

Pricing

$49.99
Original price of ~~$119.99~~
or 5 payments of $10.00

Note:

Only 7 left

♥ SAVE CHANGES
Journee Collection Womens Tru Comfort Foam Islana Bootie
Journee Collection Womens Tru Comfort Foam Islana Bootie

Pricing

$68.89
Original price of ~~$109.99~~
or 5 payments of $13.78

Rating

5 5.0 1

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Womens Tru Comfort Foam Jeeva Bootie
Journee Collection Womens Tru Comfort Foam Jeeva Bootie

Pricing

$89.99 or 5 payments of $18.00

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Womens Tru Comfort Foam Kaydia Bootie
new! Journee Collection Womens Tru Comfort Foam Kaydia Bootie

Pricing

$109.99 or 5 payments of $22.00

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Womens Tru Comfort Foam Tatiana Bootie
new! Journee Collection Womens Tru Comfort Foam Tatiana Bootie

Pricing

$119.99 or 5 payments of $24.00

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Women's Tru Comfort Foam Wide Width Elitta Bootie
Journee Collection Women's Tru Comfort Foam Wide Width Elitta Bootie

Pricing

$84.99 or 5 payments of $17.00

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Women's Tru Comfort Foam Kassia Bootie
Journee Collection Women's Tru Comfort Foam Kassia Bootie

Pricing

$62.53
Original price of ~~$89.99~~
or 5 payments of $12.51

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Womens Tru Comfort Foam Jentry Bootie
Journee Collection Womens Tru Comfort Foam Jentry Bootie

Pricing

$89.99 or 5 payments of $18.00

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Womens Tru Comfort Foam Maxxie Bootie
Journee Collection Womens Tru Comfort Foam Maxxie Bootie

Pricing

$64.70
Original price of ~~$89.99~~
or 5 payments of $12.94

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Women's Tru Comfort Foam Vista Bootie
Journee Collection Women's Tru Comfort Foam Vista Bootie

Pricing

$109.99 or 5 payments of $22.00

Note:

Free Shipping

♥ SAVE CHANGES
Journee Collection Womens Tessa Bootie
Journee Collection Womens Tessa Bootie

Pricing

$99.99 or 5 payments of $20.00

Note:

Free Shipping

♥ SAVE CHANGES

Rosalie Leather Ankle Boots

SAINT G Rosalie women's ankle boots. Sizes: 6/36,7/37,8/38,9/39,10/40,11/41. Black, cuoio, off-white lining, sole, and insole. Pointed toe boots Slip-on Approx. 1.5" heel Approx. 1.5" platform Breathable PU, EVA Synthetic stretch Nappa material

buy now
Naja Stretch Ankle Bootie with Memory Foam

Perfect for transitioning through the seasons, the new Naja by Impo is our "most-wanted" ankle boot. Classic and comfortable, these popular booties are crafted from sustainable eco faux suede or vegan faux leather and are available in a wide range of colors. This stylish stretch bootie is sculpted w

buy now
Impo Naja Chain II Stretch Ankle Bootie with Memory Foam

With a return to celebration and sparkle, glam it up in sparkly, bejeweled, dress-up fashion! The Naja Chain II by Impo is a glamorous take on the most-wanted ankle boot in the collection. Elevated by an eye-catching metallic chain with crystal stones, this popular bootie is crafted from sustainable

buy now
Impo Naja Sequin Stretch Ankle Bootie with Memory Foam

Impo's popular Naja ankle boot is crafted from velvet and scattered in scintillating sequins to emulate stars and solar rays as the light playfully bounces off the sequins! Style them to elevate a tailored edit for an evening occasion, or a minimal outfit to bring an upbeat spirit for an early eve

buy now
Elicia Chain Stretch Ankle Bootie with Memory Foam

The Elicia Chain is a pointed toe boot that is topped off with a chunky polished goldtone or silvertone chain, has a stretch opening, and rests on an elegant kitten heel. Wear yours with an oversized cardigan, matching turtleneck sweater, and cropped denim. Pointed toe Inside zipper A

buy now
Orval Stretch Platform Boot with Memory Foam

The Orval knee-high boot is an updated version of an Impo fav. This elegant boot is crafted from our eco-friendly faux suede, features a wafer platform, modern block heel, a feminine knotted ankle wrap and is topped off with an artfully designed ornament. Choose them as the refined finish to a prin

buy now
Ovidia Stretch Platform Boot with Memory Foam

The Ovidia knee-high boot is an updated version of an Impo fav! This elegant boot is crafted from our eco-friendly faux suede, features a wafer platform, fashionable slim block heel, a modern looped ankle wrap, and is topped off with an artfully designed crescent rope metallic ornament. Choose them

buy now
Ovidia Bling Stretch Platform Boot with Memory Foam

With a return to celebration and sparkle, glam it up in sparkly, bejeweled, dress-up fashion with the Ovidia Bling Boot. This party-ready boot is crafted from our eco-friendly faux suede, features a wafer platform, fashionable slim block heel, a crystal adorned ankle wrap, and is topped off with an

buy now
Orval Wide Calf Stretch Platform Boot with Memory Foam

The Orval wide calf knee-high boot is an updated version of an Impo fav. This elegant boot is crafted from our eco-friendly faux suede, features a wafer platform, modern block heel, a feminine knotted ankle wrap and is topped off with an artfully designed ornament. Choose them as the refined finish

buy now
Naturalizer Madalynn Gore Water-Repellant Ankle Bootie

Take on rainy days and Mondays with confidence and style. This water-repellant ankle boot from Naturalizer includes a stretch gore panel at the side for a flexible fit, thermal sock liner to keep your foot warm and a lug sole for superior grip.

buy now
Noeva Stretch Knit Ankle Bootie with Memory Foam

The Noeva bootie is designed for comfortable all-day wear! They're crafted from soft sweater-like knit, with an almond toe, and rest on an elevated block heel. They can be slipped on and off with ease. Consider layering these with an oversized sweater and cropped wide-legged trousers. Pointed

buy now
Patrizia Boots Obelia

Trendy tall boot featuring a decorative ankle strap with a square metal buckle and incorporated stretch elastic back shaft panel all on a chunky and sculpted heel. Vegan-friendly materials, tonal stitching. -Full length inside zipper with a antiqued metal zipper pull. Round toe Heel

buy now
"As Is" Naturalizer Madalynn Gore Water-Repellant Ankle Bootie

Naturalizer Madalynn Gore Water-Repellant Ankle Bootie Take on rainy days and Mondays with confidence and style. This water-repellant ankle boot from Naturalizer includes a stretch gore panel at the side for a flexible fit, thermal sock liner to keep your foot warm and a lug sole for superior grip

buy now
Donald J. Pliner Abbie Faux Leather Ankle Bootie

Sleek nappa stretch faux leather, a bold block heel and western-inspired silhouette add edgy style to this easy-to-wear ankle bootie from Donald Pliner.

buy now
Journee Collection Women's Tru Comfort Foam Chayse Bootie

A fall go-to every minimalist needs, the Chayse booties by Journee Collection. This classic Chelsea silhouette features stretch gore at the ankles and a 4 mm Tru Comfort Foam insole for comfort and support. Vegan leather and a round-toe finish this sleek design. Heel Height:1 1/2-inch Heel Type: St

buy now
Tashra II Hidden Platform Wedge Bootie with Memory Foam

Our stretch booties are known for their flawless fit, and the Tashra II ankle boot delivers just that. They are precisely crafted from stretch-infused eco faux suede, pleated upper, round toe, back zip, combined with the fashionable look of sock boots and the functionality of an easy-to-wear hidden

buy now
Naturalizer Sampson Bootie

A classic has arrived. You can never go wrong with an easy-going Chelsea boot with elastic goring for a flexible fit. Get there beautifully. Contour and comfort technology for a premium fit and all-day comfort experience. Consciously packaged: 100% of these shoe boxes are made of 80% recycled paper

buy now
Naturalizer Genn-Swerve Bootie

The new dress code. With a seamless and deconstructed fit, this wear-everywhere ankle bootie with stretch features adds the finishing touch to any look you put together. Wear what moves you. All-day ankle bootie with sporty bottom. Manmade upper with a closed round toe. Side goring panel for extra f

buy now
Vance Co. Men's Marshon Chelsea Boot

With a 6 mm Tru Comfort Foam insole, this classic boot is sure to be a home run. The Marshon by Vance Co. is a classic Chelsea boot with stretch gore panels and vegan leather uppers. A durable rubber sole and pull-tab at the ankle finish the design. Pull-on Boot, Round Toe Heel Height:1-

buy now
Thomas & Vine Men's Nash Wingtip Chelsea Boot

A durable design with dapper details, the Nash by Thomas & Vine. This ankle-high boot is crafted with rich genuine leather accented by a wingtip element enhanced with brogue and medallion embellishments. Stretch gore paneling at the shaft provides a forgiving fit and a lightweight EVA outsole lined

buy now
Journee Collection Womens Tru Comfort Foam Riplee Bootie

A fall essential with details borrowed from the 70s. This ankle-high silhouette features soft vegan leather uppers grounded by a block heel and a chunky treaded sole. A 4 mm Tru Comfort Foam™ footbed makes them fit like a dream, and stretch gore at the ankles makes them easy to slip on. At Journee C

buy now
Journee Collection Womens Tru Comfort Foam Estee Bootie

We're swooning for combat booties this season. The Estee bootie by Journee Collection features an exposed zipper at the vamp highlighted by soft vegan leather uppers that rise above the ankles. A knit panel at the ankle and a 4 mm Tru Comfort Foam™ footbed offer all-day comfort, and a block heel pai

buy now
Journee Collection Womens Tru Comfort Foam Islana Bootie

A sassy spin on the Chelsea bootie, the Islana by Journee Collection. These modern booties feature supple vegan leather uppers detailed with a chunky block heel and a treaded platform sole. A 4mm Tru Comfort Foam™ insole makes them comfy to walk in, and twin stretch gore panels at the ankle make the

buy now
Journee Collection Womens Tru Comfort Foam Jeeva Bootie

The boot for every activity. The Jeeva by Journee Collection is a high-low bootie crafted with our signature vegan leather supported by a grippy lug sole. An inside zipper offers easy entry, and a stretch panel at the ankle paired with a 4 mm Tru Comfort Foam™ footbed provides a super comfortable fi

buy now
Journee Collection Womens Tru Comfort Foam Kaydia Bootie

Your outfit possibilities are endless with a mix-and-matchable bootie like the Kaydia by Journee Collection. This classic Chelsea bootie is crafted with soft leather uppers accented by stretch gore at the ankles. A 4 mm, Tru Comfort Foam™ insole makes them a breeze to walk in, and a square-toe offer

buy now
Journee Collection Womens Tru Comfort Foam Tatiana Bootie

This chelsea bootie is so comfy and cute that you'll want to wear them all season long. The Tatiana by Journee Collection is a classic Chelsea style featuring vegan leather elevated by a lug sole and block heel. Stretch gore at the ankles and a supportive 4mm Tru Comfort Foam™ insole perfect the fit

buy now
Journee Collection Women's Tru Comfort Foam Wide Width Elitta Bootie

You'll find yourself wearing the comfortable but classic Elitta bootie by Journee Collection everywhere. This wide-width chelsea bootie features stretch gore panels at the ankles, soft vegan leather uppers, and a supportive 4 mm Tru Comfort Foam footbed for the perfect fit. A pointed toe and an hour

buy now
Journee Collection Women's Tru Comfort Foam Kassia Bootie

Pull them on and go, the Kassia by Journee Collection. This combat bootie features soft vegan leather, the perfect ankle height, and a stacked chunky heel. The 4 mm Tru Comfort Foam footbed adds support, and a classic lace-up closure paired with a stretch panel creates an easy entry. Lace-up c

buy now
Journee Collection Womens Tru Comfort Foam Jentry Bootie

The Jentry by Journee Collection isn't your ordinary chelsea bootie. Shaped with vegan leather, this chelsea style is made to fit comfortably with a 4 mm Tru Comfort Foam™ insole and stretch panels at the ankles. A block heel elevates the design, and a round-toe finishes the look. Heel Height: appro

buy now
Journee Collection Womens Tru Comfort Foam Maxxie Bootie

In the Maxxie bootie by Journee Collection, the outfit possibilities are endless. These booties feature vegan leather uppers that rise to the ankles and highlight a square-toe detail. Flexible stretch gore makes them easy to pull on, and a 4 mm Tru Comfort Foam™ insole makes them super comfortable.

buy now
Journee Collection Women's Tru Comfort Foam Vista Bootie

Indulge in a bold new look with the Vista by Journee Collection. This chelsea bootie adds a modern finish to your look with a lug sole and two-tone details. A dreamy 6 mm Tru Comfort Foam™ insole makes them super comfortable, and stretch gore accents at the ankles make them easy to pull on, even on

buy now
Journee Collection Womens Tessa Bootie

Tessa is the perfect distressed look for this season. The almond toe, chunky heel, and the scalloped edges to top it all off. The open ankle design adds a beautiful touch to a feminine bootie. Pair with your favorite skinnies or a dress for the perfect look. Medium width. Inside zip, stretch

buy now