Best Seller
WIDE FIT Jackie Lace Up Ankle Boot - black

WIDE FIT Jackie Lace Up Ankle Boot - black

Walk it out in confidence with the Jackie Lace Up Ankle Boot. These black boots are must-haves with their quilted detailing and chunky heels. A lace-up style with a convenient side zip, you'll be comfortable all day long in this wide fit.Key Features... more

$109.99 $76.99

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WIDE FIT Melda Ankle Boot - black

WIDE FIT Melda Ankle Boot - black

You'll love how our Melda Ankle Boot instantly elevates your look. This classic boot silhouette features a block heel, textured faux leather fabrication, an exposed zip detail, and an easy inner zip closure.Key Features Include:- Almond toe- Exposed... more

$109.99 $76.99

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Best Seller
WIDE FIT Valentina Ankle Boot - black

WIDE FIT Valentina Ankle Boot - black

Introducing our versatile footwear, the Valentina Ankle Boot. Designed with cushioned insoles for maximum support, they are perfect for pairing with any outfit. Key Features Include:- Round toe ankle boot- Wide width fit- Side zip closure- Cushioned... more

$99.99 $69.99

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WIDE FIT Valentina Ankle Boot - black

WIDE FIT Valentina Ankle Boot - black

Introducing our versatile footwear, the Valentina Ankle Boot. Designed with cushioned insoles for maximum support, they are perfect for pairing with any outfit. Key Features Include:- Round toe ankle boot- Wide width fit- Side zip closure- Cushioned... more

$99.99 $69.99

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WIDE FIT Gina Lace Up Ankle Boot - black

WIDE FIT Gina Lace Up Ankle Boot - black

Cozy with an edge! Our Gina Lace Up Ankle Boot is perfect for cold weather days. With its round toe and wide fit, you'll be comfortable all day long. The faux fur lining makes this boot look as comfortable as it feels!Key Features Include:- Round toe-... more

$109.99 $76.99

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WIDE FIT Kylee Quilted Ankle Boot - black

WIDE FIT Kylee Quilted Ankle Boot - black

This luxurious boot features quilted detail and a rounded toe for a classic, chic look. The side buckle and low block heel also add just the right amount of flair to your footwear!Key Features Include:- Rounded toe- Side buckle detail- Low block heel-... more

$109.99 $76.99

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WIDE FIT Saige Ankle Boot - black

WIDE FIT Saige Ankle Boot - black

The low block heel, faux fur trim, and treaded sole of our Saige Ankle Boot make it the ideal addition to your footwear that you'll be reaching for all season long. The wide fit also keeps you comfortable all day long. Key Features Include:- Round toe-... more

$109.99 $76.99

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WIDE FIT Rita Ankle Boot - black

WIDE FIT Rita Ankle Boot - black

The Rita Ankle Boot is the perfect combination of style and comfort to keep you strutting all season long. You'll feel right at ease in the wide fit of this ankle boot with a supportive block heel.Key Features Include:- Round toe ankle boot- Wide width... more

$109.99 $76.99

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WIDE FIT Rita Ankle Boot - black

WIDE FIT Rita Ankle Boot - black

The Rita Ankle Boot is the perfect combination of style and comfort to keep you strutting all season long. You'll feel right at ease in the wide fit of this ankle boot with a supportive block heel.Key Features Include:- Round toe ankle boot- Wide width... more

$109.99 $76.99

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WIDE FIT Valentina Ankle Boot - black

WIDE FIT Valentina Ankle Boot - black

Introducing our versatile footwear, the Valentina Ankle Boot. Designed with cushioned insoles for maximum support, they are perfect for pairing with any outfit. Key Features Include:- Round toe ankle boot- Wide width fit- Side zip closure- Cushioned... more

$99.99 $69.99

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WIDE FIT Saige Ankle Boot - black

WIDE FIT Saige Ankle Boot - black

The low block heel, faux fur trim, and treaded sole of our Saige Ankle Boot make it the ideal addition to your footwear that you'll be reaching for all season long. The wide fit also keeps you comfortable all day long. Key Features Include:- Round toe-... more

$109.99 $76.99

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WIDE FIT Eliana Ankle Boot - black

WIDE FIT Eliana Ankle Boot - black

Simplicity, comfort, and endless style come together in the faux suede fabrication of our Eliana Ankle Boot. The wide fit, mid block heel, and ankle boot style ensure your comfort throughout the day. Key Features Include:- Round toe- Ankle boot design-... more

$109.99 $76.99

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WIDE FIT Valentina Ankle Boot - black

WIDE FIT Valentina Ankle Boot - black

Introducing our versatile footwear, the Valentina Ankle Boot. Designed with cushioned insoles for maximum support, they are perfect for pairing with any outfit. Key Features Include:- Round toe ankle boot- Wide width fit- Side zip closure- Cushioned... more

$99.99 $69.99

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Stef Chelsea Ankle Boots

Stef Chelsea Ankle Boots

Men's Ann Demeulemeester Stef Chelsea Ankle Boots - Black - Casual boots Synonymous with timeless elegance, the Chelsea boot gets a low-key update from Ann Demeulemeester. A menswear classic, they will go with a navy or grey suit, or with jeans and a... more

$796.18 $489.17

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WIDE FIT Briella Ankle Boot - black

WIDE FIT Briella Ankle Boot - black

We love the metallic detail of our Briella Ankle Boot! Whether you're pairing it with a biker jacket and its exposed zips, or styling it in your everyday wear, this style's a winner!Key Features Include:- Side zip closure- Round toe- Low block heel-... more

$109.99 $76.99

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Men's Daily Double Chelsea Boots by Eastland® in Black (Size 13 M)

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 13 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

$125.00

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 14 W)

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 14 W)

These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more

$90.99 $69.99

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 11 1/2 W)

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 11 1/2 W)

These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more

$90.99 $69.99

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Henry Country Ankle Chelsea Boot

Henry Country Ankle Chelsea Boot

Men's Tricker's Henry Country Ankle Chelsea Boot - Brown - Casual boots 100% Leather. Made in Italy. more

$732.05 $597.36

FREE shipping

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Larue Chelsea Ankle Boots

Larue Chelsea Ankle Boots

Men's Moncler Larue Chelsea Ankle Boots - Blue - Casual boots Larue Chelsea ankle boots in leather. Round toe Elasticated side panels Rear pull tab Rear logo ring Embossed logo at midsole Debossed logo at heel cap. 100% Leather. more

$795.00

FREE shipping

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Men's Daily Double Chelsea Boots by Eastland® in Black (Size 9 1/2 M)

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 9 1/2 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

$125.00

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Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 12 M)

Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 12 M)

These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more

$90.99 $69.99

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Men's Daily Double Chelsea Boots by Eastland® in Black (Size 11 1/2 M)

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 11 1/2 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

$125.00

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 9 1/2 W)

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 9 1/2 W)

These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more

$90.99 $69.99

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Chelsea Ankle Boots

Chelsea Ankle Boots

Men's Tod's Chelsea Ankle Boots - Brown - Casual boots 100% Suede, 100% Rubber. Made in Italy. more

$587.78 $479.63

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Slip-on Chelsea Ankle Boots

Slip-on Chelsea Ankle Boots

Men's Tod's Slip-on Chelsea Ankle Boots - Brown - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 1.5cm 100% Calf Leather, 100% Rubber. Made in Italy. more

$694.65 $566.83

FREE shipping

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Black Show Chelsea Boots

Black Show Chelsea Boots

Men's Givenchy Black Show Chelsea Boots - Casual boots Ankle-high brushed bullskin Chelsea boots in black. more

$1,095.00 $548.00

FREE shipping

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Black O-ring Chelsea Boots

Black O-ring Chelsea Boots

Men's Marni Black O-ring Chelsea Boots - Casual boots Ankle-high patent leather Chelsea boots in black. more

$1,250.00 $850.00

FREE shipping

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Black 2976 Gothic Americana Quad Chelsea Boots

Black 2976 Gothic Americana Quad Chelsea Boots

Men's Dr. Martens Black 2976 Gothic Americana Quad Chelsea Boots - Casual boots Ankle-high polished leather Chelsea boots in black. more

$210.00

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Urban Outfitters Shoes | Black Urban Outfitters Chelsea Ankle Boots. Size 8. Fair Condition. | Color: Black | Size: 8

Urban Outfitters Shoes | Black Urban Outfitters Chelsea Ankle Boots. Size 8. Fair Condition. | Color: Black | Size: 8

Black Urban Outfitters Ankle Boots In Size 8. Fit True To Size. These Are In Fair Condition With Some Scuffs, Peeling (Especially On Right Boot), And Bending From Wear. The Heels And Bottoms Are In Great Condition. Please Zoom Into Pictures And Reach... more

$9.00

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Free People Shoes | Free People James Black Leather Chelsea Heeled Ankle Boot Nwot | Color: Black | Size: 11

Free People Shoes | Free People James Black Leather Chelsea Heeled Ankle Boot Nwot | Color: Black | Size: 11

Free People James Black Leather Chelsea Heeled Ankle Boot Nwot Sz 41 Make Me An Offer! Special Discounts Available For Bundles Of 2 Items Or More! Questions? Leave A Comment Below! more

$125.00

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Gucci Shoes | Gucci Boots Mens Chelsea Ankle Black Leather Logo Hardware Sz 11 11.5 | Color: Black | Size: 11.5

Gucci Shoes | Gucci Boots Mens Chelsea Ankle Black Leather Logo Hardware Sz 11 11.5 | Color: Black | Size: 11.5

Designer: Gucci Size: Marked As 11 / Us 11.5 (Conversion Per Designer's Website) Condition: Authentic And Brand New Style Name / Number: 624661 Cdzk0 1000 Material: Leather Upper, Leather Unique Features: Classic Black Leather Mens Chelsea Ankle Boots.... more

$599.00

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Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8 | Color: Black/Cream | Size: 8

Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8 | Color: Black/Cream | Size: 8

New With Box Size 38.5 / Us 8.5 Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side... more

$170.00

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Free People Shoes | Free People Arlo Santa Fe Ankle Chelsea Boots Black Crocodile Snake Size 7 | Color: Black | Size: 7

Free People Shoes | Free People Arlo Santa Fe Ankle Chelsea Boots Black Crocodile Snake Size 7 | Color: Black | Size: 7

Free People Arlo Santa Fe Ankle Boots Size: European 37.5 (Us 7) Color: Black Crocodile Basically Brand New. Sales Sticker Still On Sole. Only Worn Once. Condition: These Shoes Are Intentionally Distressed. Brand New, They Intentionally Look Worn In,... more

$80.00

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Kate Spade Shoes | Kate Spade New York Edimburg Black Chelsea Ankle Rain Boot New | Color: Black/Gold | Size: 11

Kate Spade Shoes | Kate Spade New York Edimburg Black Chelsea Ankle Rain Boot New | Color: Black/Gold | Size: 11

Kate Spade New York Edimburg Black Chelsea Ankle Rain Boot New Size 11 New Without Original Box Approx 1-1/2" Heel Round-Toe Pull-On Boots With Goring At Sides Gold-Tone Piping At Welt Back Heel Tab Upper And Outer Sole: Polyvinyl Chloride; Inner... more

$109.00

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Free People Shoes | Free People "Atlas" Black Puffer And Leather Chelsea Ankle Boot / Bootie | Color: Black/Gold | Size: 9.5 Us / 39.5 Eu

Free People Shoes | Free People "Atlas" Black Puffer And Leather Chelsea Ankle Boot / Bootie | Color: Black/Gold | Size: 9.5 Us / 39.5 Eu

Free People "Atlas" Black Puffer And Leather Chelsea Ankle Boot / Bootie Say Hello To The Perfect, Most Versatile Boot. The Ankle Height Makes This Style Easily Transition From Day To Night. Wear Them With Your Favorite Skinny Jeans And Tee For A More... more

$90.00

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Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8.5 | Color: Black/Cream | Size: 8.5

Free People Shoes | Free People James Chelsea Black Boots Chunky Feels Ankle Booties 38.5 Us 8.5 | Color: Black/Cream | Size: 8.5

New With Box Size 38.5 / Us 8.5 Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side... more

$180.00

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Coach Shoes | Coach X Tabitha Simmons Velvet Black Chelsea Hiker Ankle Boots | Color: Black | Size: 8

Coach Shoes | Coach X Tabitha Simmons Velvet Black Chelsea Hiker Ankle Boots | Color: Black | Size: 8

Coach X Tabitha Simmons Velvet Black Chelsea Ankle Booties Velvet Upper Man-Made Leather Lining And Footbed Rubber Outsole Zip Closure Shaft: 4 1/2" Height, 9" Circumference 1" Heel This Special Collaboration Between Coach And Designer Tabitha Simmons... more

$149.00

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Free People Shoes | Free People Atlas Chelsea Puffer Ankle Boots Black Size 8.5 38.5 New | Color: Black | Size: 8.5

Free People Shoes | Free People Atlas Chelsea Puffer Ankle Boots Black Size 8.5 38.5 New | Color: Black | Size: 8.5

Reposhing This Item I Purchased From @Jgsgmma. Loved It, Just Need A Half Size Smaller! more

$50.00

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Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8

Free People Shoes | Black Free People Ankle Chelsea Boot | Color: Black | Size: 8

There Are A Euro Size 41 (Us 8) Free People Cowboy/ Chelsea Boot Style Stretchy On The Side Like A Chelsea Boot Small Heel more

$45.00

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