Best Seller
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 9.5

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 9.5

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

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Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 11.5

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 11.5

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

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Best Seller
Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 13

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 13

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

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Killington Chukka Boots - Black - Timberland Boots

Killington Chukka Boots - Black - Timberland Boots

Men's Timberland Killington Chukka Boots - Black - Casual boots Men's Timberland boots with premium full-grain leather uppers from a Leather Working Group Silver-rated sustainable tannery. Showcasing an iconic, chukka boot silhouette, the lightweight,... more

$170.00 $86.00

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Nunn Bush Otto Plain Toe Chukka - Mens 9.5 Grey Boot XW

Nunn Bush Otto Plain Toe Chukka - Mens 9.5 Grey Boot XW

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

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Nunn Bush Otto Plain Toe Chukka - Mens 9 Grey Boot W

Nunn Bush Otto Plain Toe Chukka - Mens 9 Grey Boot W

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

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Nunn Bush Otto Plain Toe Chukka - Mens 12 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 12 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

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Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 11 1/2 4W)

Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 11 1/2 4W)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 8 1/2 6E)

Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 8 1/2 6E)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Men's Murphy Casual Boots by Drew in Camel Leather (Size 15 6E)

Men's Murphy Casual Boots by Drew in Camel Leather (Size 15 6E)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. The... more

$286.99

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Columbia Granite Trails Mid WP Hiking Boots Leather/Synthetic Men's, Dark Gray/Raw Honey SKU - 320900

Columbia Granite Trails Mid WP Hiking Boots Leather/Synthetic Men's, Dark Gray/Raw Honey SKU - 320900

The Columbia Granite Trails Mid WP Hiking Boot is a lightweight hiker with the versatility and comfort you need to go from town to the local hill and everywhere in between. Its waterproof, breathable, and supportive, with plush cushioning and a grippy... more

$89.95 $67.46

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Danner Riverside 4.5" Work Boots Leather Men's, Brown/Green SKU - 509263

Danner Riverside 4.5" Work Boots Leather Men's, Brown/Green SKU - 509263

The Danner Riverside Leather Work Boots have a durable leather and textile upper with Danner Dry waterproof protection. This athletic design offers cushioning support from the lightweight EVA footbed and shock-absorbing EVA midsole. These boots are... more

$184.95

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Columbia Granite Trails Mid WP Hiking Boots Leather/Synthetic Men's, Dark Gray/Raw Honey SKU - 141438

Columbia Granite Trails Mid WP Hiking Boots Leather/Synthetic Men's, Dark Gray/Raw Honey SKU - 141438

The Columbia Granite Trails Mid WP Hiking Boot is a lightweight hiker with the versatility and comfort you need to go from town to the local hill and everywhere in between. Its waterproof, breathable, and supportive, with plush cushioning and a grippy... more

$89.95 $67.46

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Jimmy Chukka Boot

Jimmy Chukka Boot

Men's Vance Co. Jimmy Chukka Boot - Gray - Casual boots Want to look impressive around the clock? Then choose the Jimmy chukka boot by Vance Co. This lace-up sneaker ensures above-par comfort levels with its Tru Comfort foam insole. EVA sole stays... more

$74.99

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HAIX Eagle Tactical FL High Waterproof Leather Boots - Men's Black 4 Wide 340035W-4

HAIX Eagle Tactical FL High Waterproof Leather Boots - Men's Black 4 Wide 340035W-4

HAIX Eagle Tactical FL High Waterproof Leather Boots - Men's Black 4 Wide 340035W-4. We are excited to introduce the Black Eagle Tactical 2.0 FL High This all-leather 8 boot features the highest quality water resistant European bull hide leather for... more

$249.00

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Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 12

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 12

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

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Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 10.5

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 10.5

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

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Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 8

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 8

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

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Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 8.5

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 8.5

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

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Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 14

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 14

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

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Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 11

Thomas and Vine Keegan Wide Width Plain Toe Chukka Boot - Grey - 11

The Keegan wide-width boot by Thomas & Vine is comfortable enough to wear to work and drinks after. This stylish round-toe chukka boot features a two-eye lace-up closure with a second pair of interchangeable laces and your choice of genuine leather or... more

$109.99

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Nunn Bush Otto Plain Toe Chukka - Mens 8.5 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 8.5 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 13 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 13 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 8 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 8 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 10.5 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 10.5 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 7 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 7 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 12 Grey Boot XW

Nunn Bush Otto Plain Toe Chukka - Mens 12 Grey Boot XW

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 13 Grey Boot W

Nunn Bush Otto Plain Toe Chukka - Mens 13 Grey Boot W

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 11 Grey Boot XW

Nunn Bush Otto Plain Toe Chukka - Mens 11 Grey Boot XW

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 7.5 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 7.5 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 11.5 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 11.5 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 8 Grey Boot W

Nunn Bush Otto Plain Toe Chukka - Mens 8 Grey Boot W

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 10 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 10 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 9.5 Grey Boot W

Nunn Bush Otto Plain Toe Chukka - Mens 9.5 Grey Boot W

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 9 Grey Boot XW

Nunn Bush Otto Plain Toe Chukka - Mens 9 Grey Boot XW

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 10 Grey Boot XW

Nunn Bush Otto Plain Toe Chukka - Mens 10 Grey Boot XW

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 11 Grey Boot Medium

Nunn Bush Otto Plain Toe Chukka - Mens 11 Grey Boot Medium

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 10 Grey Boot W

Nunn Bush Otto Plain Toe Chukka - Mens 10 Grey Boot W

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 10.5 Grey Boot XW

Nunn Bush Otto Plain Toe Chukka - Mens 10.5 Grey Boot XW

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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Nunn Bush Otto Plain Toe Chukka - Mens 10.5 Grey Boot W

Nunn Bush Otto Plain Toe Chukka - Mens 10.5 Grey Boot W

*This Chukka boot has the style and comfort to dress up any look! *Smooth or suede leather upper with Defender Repellant for water-and stain resistance *Flex Technology for comfort *Removable molded EVA with Memory Foam footbed *Lightweight EVA and... more

$89.95 $46.97

FREE shipping

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More information about Men's Shoes

Best prices on Leather chukka boots, Lightweight, Gray 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.