Best Seller
'made In England' 2976 Vintage Chelsea Boots

'made In England' 2976 Vintage Chelsea Boots

Men's Dr. Martens 'made In England' 2976 Vintage Chelsea Boots - Black - Formal boots Ankle-high buffed leather Chelsea boots in black. Round toe. Logo-woven webbing pull loop in black and gold-tone at heel counter. Elasticized gusset at sides. Buffed... more

$170.00

go to store
Ankle Boots

Ankle Boots

Men's Givenchy Ankle Boots - Black - Casual boots Step out in style with Givenchy's black shiny leather chelsea boots for men. These ankle boots feature side elasticated panels, a round-toe silhouette, leather lining, and a lug rubber sole. The iconic... more

$889.00 $622.30

go to store
Best Seller
Landon Boot

Landon Boot

Men's Vance Co. Landon Boot - Gray - Casual boots The Landon Chelsea-inspired ankle boot from Vance Co is a staple to add to your winter wardrobe. Faux leather upper. Dual elastic gores. Burnished round toe. Fabric lining. Synthetic sole. more

$64.99

go to store
Coach Shoes | Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d | Color: Brown | Size: 8.5

Coach Shoes | Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d | Color: Brown | Size: 8.5

Coach Mens Chelsea Boots Ankle Suede Pull-On Round Toe Leather Insole Brown 8.5d Pull On Round Toe Features A Comfortable Crepe Sole Ribbed Ankle Gores Pull Tab For On-And-Off Ease. Style No. G2290 Suede Upper Leather Lining And Footbed Rubber Outsole... more

$69.00

go to store
Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

Madewell Shoes | - Madewell Chelsea Tan Slip On Ankle Boots Sz 9 | Color: Tan | Size: 9

Tan Leather With Elastic Stretch On Both Side For Easy Slip On Round Toe Leather Sole Preowned But In Good Condition more

$65.00

go to store
Madewell Shoes | Madewell Lonny Leather Black Heeled Chelsea Ankle Boots Size 9 | Color: Black | Size: 9

Madewell Shoes | Madewell Lonny Leather Black Heeled Chelsea Ankle Boots Size 9 | Color: Black | Size: 9

Details Round-Toe Madewell Booties Have Easy Pull-On Style With Exposed Elastic Gores Detailing The Short Shaft. Stacked Heel And Rubber Sole. Leather: Calfskin. Measurements Heel: 3.5in more

$49.00

go to store
Burton Mens Suede Chelsea Ankle High Boots - Brown - Brown - 13

Burton Mens Suede Chelsea Ankle High Boots - Brown - Brown - 13

- Elasticated gusset, pull tab - Square - Cut: Ankle high - Design: Plain - Toe style: Round - Fit: Regular - Fastening: Slip-on more

$144.99 $72.20

go to store
Burton Mens Suede Chelsea Ankle High Boots - Brown - Brown - 9

Burton Mens Suede Chelsea Ankle High Boots - Brown - Brown - 9

- Elasticated gusset, pull tab - Square - Cut: Ankle high - Design: Plain - Toe style: Round - Fit: Regular - Fastening: Slip-on more

$144.99 $69.95

go to store
Burton Mens Suede Chelsea Ankle High Boots - Black - Black - 7

Burton Mens Suede Chelsea Ankle High Boots - Black - Black - 7

- Elasticated gusset, pull tab. - Square. - Cut: Ankle high. - Design: Plain. - Toe style: Round. - Fit: Regular. - Fastening: Slip-on. more

$144.99 $43.20

go to store
Sahara Block Heel Chelsea Boot - Black - Paul Green Boots

Sahara Block Heel Chelsea Boot - Black - Paul Green Boots

Women's Paul Green Sahara Block Heel Chelsea Boot - Black - Ankle boots A treaded sole and stacked block bring a touch of edge to this round-toe Chelsea boot featuring flexible hidden gore insets and a side zip for easy on and off. 3 1/4" heel; 3/4"... more

$520.00 $360.00

FREE shipping

go to store
Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Medium Brown 10.5 GB00353-105M

Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Medium Brown 10.5 GB00353-105M

Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Medium Brown 10.5 GB00353-105M. The new Georgia Boot AMP LT Wedge Work Boots start out with durable pasture proof SPR leather just like their classic wedges but then we pack on... more

$187.00

FREE shipping

go to store
Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Wide Brown 10.5 GB00353-105W

Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Wide Brown 10.5 GB00353-105W

Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Wide Brown 10.5 GB00353-105W. The new Georgia Boot AMP LT Wedge Work Boots start out with durable pasture proof SPR leather just like their classic wedges but then we pack on the... more

$187.00

FREE shipping

go to store
Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 W)

Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 W)

A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

$89.95

go to store
Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (Size 11 1/2 W)

Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (Size 11 1/2 W)

A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

$89.95

go to store
Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (Size 11 1/2 EW)

Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (Size 11 1/2 EW)

A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

$89.95

go to store
Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... more

$69.99

go to store
Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot w/Steel Toe - Men's Wide Brown 10 GB00337-100W

Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot w/Steel Toe - Men's Wide Brown 10 GB00337-100W

Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot w/Steel Toe - Men's Wide Brown 10 GB00337-100W. Built with a combination cement and San Crispino construction the upper is crafted from full-grain SPR leather and features twin gore panels and... more

$170.00

FREE shipping

go to store
Blair Men's Deer Stags Rockland Chelsea Boots - Black - 10 - Womens

Blair Men's Deer Stags Rockland Chelsea Boots - Black - 10 - Womens

Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... more

$69.99

go to store
Landon Boot

Landon Boot

Men's Vance Co. Landon Boot - Brown - Casual boots The Landon Chelsea-inspired ankle boot from Vance Co is a staple to add to your winter wardrobe. Faux leather upper. Dual elastic gores. Burnished round toe. Fabric lining. Synthetic sole. more

$64.99

go to store
Landon Boot

Landon Boot

Men's Vance Co. Landon Boot - Black - Casual boots The Landon Chelsea-inspired ankle boot from Vance Co is a staple to add to your winter wardrobe. Faux leather upper. Dual elastic gores. Burnished round toe. Fabric lining. Synthetic sole. more

$64.99

go to store
Landon Boot

Landon Boot

Men's Vance Co. Landon Boot - Brown - Casual boots The Landon Chelsea-inspired ankle boot from Vance Co is a staple to add to your winter wardrobe. Faux leather upper. Dual elastic gores. Burnished round toe. Fabric lining. Synthetic sole. more

$64.99

go to store
Landon Boot

Landon Boot

Men's Vance Co. Landon Boot - Black - Casual boots The Landon Chelsea-inspired ankle boot from Vance Co is a staple to add to your winter wardrobe. Faux leather upper. Dual elastic gores. Burnished round toe. Fabric lining. Synthetic sole. more

$64.99

go to store
Landon Boot

Landon Boot

Men's Vance Co. Landon Boot - Blue - Casual boots The Landon Chelsea-inspired ankle boot from Vance Co is a staple to add to your winter wardrobe. Faux leather upper. Dual elastic gores. Burnished round toe. Fabric lining. Synthetic sole. more

$64.99

go to store
Landon Boot

Landon Boot

Men's Vance Co. Landon Boot - Brown - Casual boots The Landon Chelsea-inspired ankle boot from Vance Co is a staple to add to your winter wardrobe. Faux leather upper. Dual elastic gores. Burnished round toe. Fabric lining. Synthetic sole. more

$64.99

go to store
Free People Shoes | Free People Atlas Ankle Studded Suede Chelsea Boots Black 9.5 | Color: Black | Size: 39.5eu

Free People Shoes | Free People Atlas Ankle Studded Suede Chelsea Boots Black 9.5 | Color: Black | Size: 39.5eu

Brand - Free People Size - Eu 39.5 / Us 9.5 Excellent Preowned Condition Ankle, Chelsea, Studded Trim, Scalloped Lace Trim, Pull On, Side Stretch, Suede, Leather, Round Toe, Comfortable, Hiking, Causal, Winter, Fall, Combat, Booties more

$85.00

go to store
Kate Spade Shoes | Kate Spade New York Ankle Chelsea Boots | Color: Black | Size: 10

Kate Spade Shoes | Kate Spade New York Ankle Chelsea Boots | Color: Black | Size: 10

Kate Spade New York Ankle Chelsea Boots Black & Metallic Leather & Rubber Trim Round-Toes With Glitter Accents Heels: 1.5" Size: 10 In Good Condition, Small Spots On Boots Where Glitter Is Scratched From Being In Closet. - You Can See By The Soles... more

$28.00

go to store
Kate Spade Shoes | Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots | Color: Black/Gray | Size: 7

Kate Spade Shoes | Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots | Color: Black/Gray | Size: 7

Kate Spade Garden Gray/ Truffle Suede Scalloped Chelsea Ankle Boots Beautiful Graphite Dark Truffle Gray Slip On Style With Side Gore Panels Feminine Scallop Details Sweet Back Heel Bow Round Toe Cushioned Insole Leather Sole 3” Block Heel Made In... more

$70.00

go to store
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

go to store
J. Crew Shoes | J. Crew Black Leather Lug Sole Chunky Chelsea Boots Ankle Booties Size 8 Euc | Color: Black | Size: 8

J. Crew Shoes | J. Crew Black Leather Lug Sole Chunky Chelsea Boots Ankle Booties Size 8 Euc | Color: Black | Size: 8

J. Crew Black Leather Lug Sole Chunky Chelsea Boots Ankle Booties Size 8 Euc Excellent Like New Condition With No Flaws Round Toe Ankle-Boot Leather Flat Anti-Slip Rubber Outsole Slip-On Style Elasticized Opening Boho Outdoor Travel Combat Military... more

$75.00

go to store
Levi's Shoes | Levi's Mens Brown Goring Calico Round Toe Chelsea 11 | Color: Brown | Size: 11

Levi's Shoes | Levi's Mens Brown Goring Calico Round Toe Chelsea 11 | Color: Brown | Size: 11

Size: 11 Size Type: Regular Style: Chelsea Width: Color: Brown Pattern: Solid Occasion: Casual Details: Goring Boot Height: 5.5 Shaft Size: Ankle Toe Type: Round Insole Material: Man Made Lining Material: Man Made Outsole Material: Man Made Upper... more

$59.00

go to store
Free People Shoes | Free People Maren Mid Chelsea Boots - Tan/Black, Size Eu41/Us10, Lug Sole Nwob | Color: Brown | Size: 41eu

Free People Shoes | Free People Maren Mid Chelsea Boots - Tan/Black, Size Eu41/Us10, Lug Sole Nwob | Color: Brown | Size: 41eu

A Wardrobe Staple, These Classic Round Toe Chelsea Boots Are The Perfect Go-With-Anything Pair. Features: Pull-On Style, Mid-Calf Length, Chelsea Design, Leather Uppers, Round Toe, Elastic Ankle Inlays, Lugged Rubber Sole, Toe Cap, Pull Loops... more

$115.00

go to store
Free People Shoes | Free People Maren Mid Chelsea Boots Size 37 | Color: Brown | Size: 37

Free People Shoes | Free People Maren Mid Chelsea Boots Size 37 | Color: Brown | Size: 37

A Wardrobe Staple, These Classic Round Toe Chelsea Boots Are The Perfect Go-With-Anything Pair. Features: Pull-On Style, Mid-Calf Length, Chelsea Design, Leather Uppers, Round Toe, Elastic Ankle Inlays, Lugged Rubber Sole, Toe Cap, Pull Loops Why We <3... more

$125.00

go to store
Free People Shoes | Free People Maren Chelsea Mid Boots - Size 39 | Color: Black/Tan | Size: 39eu

Free People Shoes | Free People Maren Chelsea Mid Boots - Size 39 | Color: Black/Tan | Size: 39eu

Excellent Condition Pull-On Style Mid-Calf Length Leather Uppers Round Toe Elastic Ankle Inlays Lugged Rubber Sole Toe Cap Pullloops Heel Height Approx. 2.5" more

$125.00

go to store
Free People Shoes | Free People Maren Mid Chelsea Boots | Color: Black/Tan | Size: 7

Free People Shoes | Free People Maren Mid Chelsea Boots | Color: Black/Tan | Size: 7

Nwob Free People Maren Mid Chelsea Boots- Size 37. A Wardrobe Staple, These Classic Round Toe Chelsea Boots Are The Perfect Go-With-Anything Pair. Features: Pull-On Style, Mid-Calf Length, Chelsea Design, Leather Uppers, Round Toe, Elastic Ankle... more

$121.00

go to store
Free People Shoes | Free People Maren Mid Chelsea Boots Size 38. Sh4 | Color: Tan | Size: 8

Free People Shoes | Free People Maren Mid Chelsea Boots Size 38. Sh4 | Color: Tan | Size: 8

Free People Maren Mid Chelsea Boots Size 38. Sh4. A Wardrobe Staple, These Classic Round Toe Chelsea Boots Are The Perfect Go-With-Anything Pair. Features: Pull-On Style, Mid-Calf Length, Chelsea Design, Leather Uppers, Round Toe, Elastic Ankle Inlays,... more

$168.00

go to store
Free People Shoes | Free People Maren Mid Chelsea Boots Size 40. Sh4 | Color: Tan | Size: 40eu

Free People Shoes | Free People Maren Mid Chelsea Boots Size 40. Sh4 | Color: Tan | Size: 40eu

Free People Maren Mid Chelsea Boots Size 40. Sh4. A Wardrobe Staple, These Classic Round Toe Chelsea Boots Are The Perfect Go-With-Anything Pair. Features: Pull-On Style, Mid-Calf Length, Chelsea Design, Leather Uppers, Round Toe, Elastic Ankle Inlays,... more

$168.00

go to store
Free People Shoes | Free People Maren Mid Chelsea Boots Size 40. Sh4 | Color: Black/Tan | Size: 10

Free People Shoes | Free People Maren Mid Chelsea Boots Size 40. Sh4 | Color: Black/Tan | Size: 10

Free People Maren Mid Chelsea Boots Size 40. Sh4. A Wardrobe Staple, These Classic Round Toe Chelsea Boots Are The Perfect Go-With-Anything Pair. Features: Pull-On Style, Mid-Calf Length, Chelsea Design, Leather Uppers, Round Toe, Elastic Ankle Inlays,... more

$139.00

go to store
Free People Shoes | Free People Maren Mid Chelsea Boots Size 38. Sh4 | Color: Black/Tan | Size: 8

Free People Shoes | Free People Maren Mid Chelsea Boots Size 38. Sh4 | Color: Black/Tan | Size: 8

Free People Maren Mid Chelsea Boots Size 38. Sh4. A Wardrobe Staple, These Classic Round Toe Chelsea Boots Are The Perfect Go-With-Anything Pair. Features: Pull-On Style, Mid-Calf Length, Chelsea Design, Leather Uppers, Round Toe, Elastic Ankle Inlays,... more

$168.00

go to store
Free People Shoes | Free People Maren Mid Chelsea Boots Size 38.5. Sh5 | Color: Black/Tan | Size: 8.5

Free People Shoes | Free People Maren Mid Chelsea Boots Size 38.5. Sh5 | Color: Black/Tan | Size: 8.5

Free People Maren Mid Chelsea Boots Size 38.5. Shoes 5 A Wardrobe Staple, These Classic Round Toe Chelsea Boots Are The Perfect Go-With-Anything Pair. Features: Pull-On Style, Mid-Calf Length, Chelsea Design, Leather Uppers, Round Toe, Elastic Ankle... more

$130.00

go to store
Free People Shoes | Free People Tate Chelsea Boot | Color: Black | Size: 6.5

Free People Shoes | Free People Tate Chelsea Boot | Color: Black | Size: 6.5

Like New Without Box Ankle Length Suede Uppers Round Toe Leather Toe Cap And Heel Tab Elastic Ankle Inlay Scalloped Trim Pull Tabs Studded Accent Tread Outsole They Have A Zippered Side Closure For Ease Of Wear And Come With Gore Panels And Pull Tabs... more

$105.00

go to store

More information about Men's Shoes

Best prices on Round toe ankle chelsea boots in Men's Shoes online. Visit Bizrate to find the best deals on top brands. Read reviews on Clothing & Accessories merchants and buy with confidence.