You're in Men's Shoes

Need a Personal Shopper?

Subscribe to
Bizrate emails for the hottest
deals & products
,
PLUS a chance to

WIN $25

sign me up!

New winners chosen weekly.
No purchase necessary.

Sperry Top-Sider Bahama Chukka Boots (For Men) ? WOOL GREY

Sperry Top-Sider Bahama Chukka Boots (For Men) ? WOOL GREY

CLOSEOUTS . The stylish wool upper is combined with generous cushioning underfoot to create the devilishly handsome Sperry Top-Sider Bahama chukka boots. Available Colors: WOOL GREY. Sizes: 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13.

at Sierra Trading Post

Sperry Top-Sider Mens Bahama Lug Chukka Bomber

Sperry Top-Sider Mens Bahama Lug Chukka Bomber

Feel secure with every step and stylish all season long when you wear this Sperry® chukka boot! Canvas upper. Genuine hand-sewn tru-moc construction for durable comfort and long-lasting style. Rust-proof metal eyelets with rawhide laces for a secure... ... more

Sperry Top-Sider Mens Bahama Lug Chukka Bomber

Feel secure with every step and stylish all season long when you wear this Sperry® chukka boot! Canvas upper. Genuine hand-sewn tru-moc construction for durable comfort and long-lasting style. Rust-proof metal eyelets with rawhide laces for a secure...

Amazon.com

$42.50

go to store
Sperry Top-Sider Men's Harbor Chukka Boot

Sperry Top-Sider Men's Harbor Chukka Boot

Leather boot featuring wool overlays, contrast welt stitching, and logo-debossed tongue Pull-tab at back Lace-up ... more

Sperry Top-Sider Men's Harbor Chukka Boot

Leather boot featuring wool overlays, contrast welt stitching, and logo-debossed tongue Pull-tab at back Lace-up

Amazon.com

$73.95

go to store
Sperry Top-Sider Men's Clipper Wool Chukka Boot

Sperry Top-Sider Men's Clipper Wool Chukka Boot

Chukka boot ... more

$84.99

go to store
Sperry Top-Sider Mens Bahama Lug Chukka Bomber

Sperry Top-Sider Mens Bahama Lug Chukka Bomber

Feel secure with every step and stylish all season long when you wear this Sperry® chukka boot! Canvas upper. Genuine hand-sewn tru-moc construction for durable comfort and long-lasting style. Rust-proof metal eyelets with rawhide laces for a secure... ... more

Sperry Top-Sider Mens Bahama Lug Chukka Bomber

Feel secure with every step and stylish all season long when you wear this Sperry® chukka boot! Canvas upper. Genuine hand-sewn tru-moc construction for durable comfort and long-lasting style. Rust-proof metal eyelets with rawhide laces for a secure...

Amazon Marketplace

$42.50

go to store
Sperry Top Sider Men's Bahama Gray Casual, Size: 8 D(M) US, Black

Sperry Top Sider Men's Bahama Gray Casual, Size: 8 D(M) US, Black

The Sperry Top Sider Bahama 2-Eye Casual Shoes feature a Canvas upper with a Moc Toe . The Vulcanized Rubber outsole lends lasting traction and wear. Size: 8 D(M) US. Color: Black. Gender: Male. Age Group: Adult. Material: Canvas. ... more

Sperry Top Sider Men's Bahama Gray Casual, Size: 8 D(M) US, Black

The Sperry Top Sider Bahama 2-Eye Casual Shoes feature a Canvas upper with a Moc Toe . The Vulcanized Rubber outsole lends lasting traction and wear. Size: 8 D(M) US. Color: Black. Gender: Male. Age Group: Adult. Material: Canvas.

Jet.com

$59.95

FREE shipping

go to store
Sperry Top Sider Men's 'Bahama 2 Eye' Basic Textile Casual Shoes, Size: 11, Grey

Sperry Top Sider Men's 'Bahama 2 Eye' Basic Textile Casual Shoes, Size: 11, Grey

Casual meets sophisticated in the varied Bahama 2 Eye shoes from Sperry Top-Sider. This boat shoe offers a number of colors and textures highlighted by nautical lacing and moc-toe stitching. The Vulcanized midsole gives shock absorbing durability and... ... more

Sperry Top Sider Men's 'Bahama 2 Eye' Basic Textile Casual Shoes, Size: 11, Grey

Casual meets sophisticated in the varied Bahama 2 Eye shoes from Sperry Top-Sider. This boat shoe offers a number of colors and textures highlighted by nautical lacing and moc-toe stitching. The Vulcanized midsole gives shock absorbing durability and...

Jet.com

$59.95

FREE shipping

go to store
Sperry Top-Sider Men's Clipper Wool Chukka Boot

Sperry Top-Sider Men's Clipper Wool Chukka Boot

Chukka boot ... more

$84.99

go to store
Sperry Top-Sider Men's Bahama Wool Boat Shoe

Sperry Top-Sider Men's Bahama Wool Boat Shoe

The classic Sperry Top-Sider boat shoe in relaxed wool top.. ... more

Sperry Top-Sider Men's Bahama Wool Boat Shoe

The classic Sperry Top-Sider boat shoe in relaxed wool top..

Amazon.com

$59.95

go to store
Sperry Top-Sider Mens Glacier Chukka Boot Black

Sperry Top-Sider Mens Glacier Chukka Boot Black

The Men's Glacier Chukka from Sperry Top Sider is designed to keep you dry and warm in the worst weather. Rugged non-marking rubber outsole with Wave-Siping for extra traction Contoured EVA midsole provides athletic-style cushioning and comfort Triple... ... more

Sperry Top-Sider Mens Glacier Chukka Boot Black

The Men's Glacier Chukka from Sperry Top Sider is designed to keep you dry and warm in the worst weather. Rugged non-marking rubber outsole with Wave-Siping for extra traction Contoured EVA midsole provides athletic-style cushioning and comfort Triple...

Amazon.com

$110.00

go to store
Sperry Top-Sider Men's Dockyard Ox Chukka Boot

Sperry Top-Sider Men's Dockyard Ox Chukka Boot

Style chukka ... more

$209.99

go to store
Sperry Top-Sider Men's Gold A/O Chukka Dark Brown Boot

Sperry Top-Sider Men's Gold A/O Chukka Dark Brown Boot

Journey into the unknown in this chukka boot, with Sperry styling and Gold Cup curation. Wear with your favorite cuffed jeans for a truly modern urban look. ... more

Sperry Top-Sider Men's Gold A/O Chukka Dark Brown Boot

Journey into the unknown in this chukka boot, with Sperry styling and Gold Cup curation. Wear with your favorite cuffed jeans for a truly modern urban look.

Amazon.com

$169.95

go to store
Sperry Top-Sider Men's Billfish Ultralite Chukka Boot

Sperry Top-Sider Men's Billfish Ultralite Chukka Boot

Leather, nubuck, and mesh upper. 360-degree lacing system. EVA midsole. Non-marking rubber outsole. Patent-pending Adaptive Wave-Siping tread ... more

Sperry Top-Sider Men's Billfish Ultralite Chukka Boot

Leather, nubuck, and mesh upper. 360-degree lacing system. EVA midsole. Non-marking rubber outsole. Patent-pending Adaptive Wave-Siping tread

Amazon.com

$119.95

go to store
Sperry Top-Sider Mens Bahama Chukka Suede Black Sneaker

Sperry Top-Sider Mens Bahama Chukka Suede Black Sneaker

This chukka features a premium suede upper and vulcanized construction with secure bonding between uppers and outsoles. Hand-sewn construction ensures longevity of wear. The Wave Comfort Foot SystemTM with removable PU footbed provides added comfort.... ... more

Sperry Top-Sider Mens Bahama Chukka Suede Black Sneaker

This chukka features a premium suede upper and vulcanized construction with secure bonding between uppers and outsoles. Hand-sewn construction ensures longevity of wear. The Wave Comfort Foot SystemTM with removable PU footbed provides added comfort....

Amazon.com

$49.99

go to store
Sperry Top-Sider Men's Harbor Chukka Boot

Sperry Top-Sider Men's Harbor Chukka Boot

Leather boot featuring wool overlays, contrast welt stitching, and logo-debossed tongue Pull-tab at back Lace-up ... more

Sperry Top-Sider Men's Harbor Chukka Boot

Leather boot featuring wool overlays, contrast welt stitching, and logo-debossed tongue Pull-tab at back Lace-up

Amazon Marketplace

$73.95

go to store
Sperry Top-Sider Men's Bahama Chukka Wool

Sperry Top-Sider Men's Bahama Chukka Wool

The Sperry Top-Sider Bahama Chukka Wool is a winterty version of the classic leather Sperry Top-Sider. The Sperry Top-Sider Bahama Chukka Wool is built on a vulcanized construction with secure bonding between uppers and outsoles. Spice up your look... ... more

Sperry Top-Sider Men's Bahama Chukka Wool

The Sperry Top-Sider Bahama Chukka Wool is a winterty version of the classic leather Sperry Top-Sider. The Sperry Top-Sider Bahama Chukka Wool is built on a vulcanized construction with secure bonding between uppers and outsoles. Spice up your look...

Amazon.com

$48.65

FREE shipping

go to store
Sperry Top Sider Men's Bristol Chukka Chukka Boot

Sperry Top Sider Men's Bristol Chukka Chukka Boot

Sperry Top Sider Men's Bristol Chukka Chukka Boot ... more

Sperry Top Sider Men's Bristol Chukka Chukka Boot

Sperry Top Sider Men's Bristol Chukka Chukka Boot

Amazon.com

$120.00

go to store
Sperry Bahama Chukka Mens Suede Boat Boots - Shoes - Burgundy

Sperry Bahama Chukka Mens Suede Boat Boots - Shoes - Burgundy

NEW SPERRY BAHAMA CHUKKA MENS LEATHER BOAT BOOTS - SHOES The Bahama Chukka Desert boot - shoe are made from a soft suede and are finished with brass eyelets, leather laces, and feature the boat lace detail like the original boat sperry They have a... ... more

Sperry Bahama Chukka Mens Suede Boat Boots - Shoes - Burgundy

NEW SPERRY BAHAMA CHUKKA MENS LEATHER BOAT BOOTS - SHOES The Bahama Chukka Desert boot - shoe are made from a soft suede and are finished with brass eyelets, leather laces, and feature the boat lace detail like the original boat sperry They have a...

Amazon.com

$42.25

FREE shipping

go to store
Sperry Top-Sider Men's Bahama Lug Chukka Casual Shoe

Sperry Top-Sider Men's Bahama Lug Chukka Casual Shoe

Feel secure with every step and stylish all season long when you wear the Sperry Bahama Lug Chukka Cloth shoe!. ... more

Sperry Top-Sider Men's Bahama Lug Chukka Casual Shoe

Feel secure with every step and stylish all season long when you wear the Sperry Bahama Lug Chukka Cloth shoe!.

Amazon.com

$42.50

go to store
Sperry Top-Sider Men's Striper Chukka Suede Boots, Brown

Sperry Top-Sider Men's Striper Chukka Suede Boots, Brown

Durable suede uppers provide incredible comfort. Vulcanized construction with secure bonding between uppers and outsoles. New Chukka pattern with padded collar provides added stability. Wave Comfort Foot System with PU removable footbed enhances... ... more

Sperry Top-Sider Men's Striper Chukka Suede Boots, Brown

Durable suede uppers provide incredible comfort. Vulcanized construction with secure bonding between uppers and outsoles. New Chukka pattern with padded collar provides added stability. Wave Comfort Foot System with PU removable footbed enhances...

Amazon.com

$46.99

go to store
Sperry Top-Sider Men's Boat Oxford Chukka Boot

Sperry Top-Sider Men's Boat Oxford Chukka Boot

Sperry Top-Sider Men's Boat Oxford Chukka Boot. The Sperry Top-Sider Boat Oxford Chukka Boot in Tan The Boat Oxford Chukka Boot is a versatile boot for day or night. It features a leather upper, tonal stitching, and a distressed look. Pair these with... ... more

Sperry Top-Sider Men's Boat Oxford Chukka Boot

Sperry Top-Sider Men's Boat Oxford Chukka Boot. The Sperry Top-Sider Boat Oxford Chukka Boot in Tan The Boat Oxford Chukka Boot is a versatile boot for day or night. It features a leather upper, tonal stitching, and a distressed look. Pair these with...

Amazon.com

$94.95

go to store
Sperry Top-Sider Men's AO Cyclone Chukka Boot

Sperry Top-Sider Men's AO Cyclone Chukka Boot

Boat shoe-inspired chukka boot featuring moccasin toe and rawhide lacing ... more

Sperry Top-Sider Men's AO Cyclone Chukka Boot

Boat shoe-inspired chukka boot featuring moccasin toe and rawhide lacing

Amazon.com

$99.95

go to store
Sperry Top-Sider Men's Bahama Chukka Wool

Sperry Top-Sider Men's Bahama Chukka Wool

The Sperry Top-Sider Bahama Chukka Wool is a winterty version of the classic leather Sperry Top-Sider. The Sperry Top-Sider Bahama Chukka Wool is built on a vulcanized construction with secure bonding between uppers and outsoles. Spice up your look... ... more

Sperry Top-Sider Men's Bahama Chukka Wool

The Sperry Top-Sider Bahama Chukka Wool is a winterty version of the classic leather Sperry Top-Sider. The Sperry Top-Sider Bahama Chukka Wool is built on a vulcanized construction with secure bonding between uppers and outsoles. Spice up your look...

Amazon Marketplace

$48.65

FREE shipping

go to store
Sperry Top-Sider Men's Bahama Lug Chukka Casual Shoe

Sperry Top-Sider Men's Bahama Lug Chukka Casual Shoe

Feel secure with every step and stylish all season long when you wear the Sperry Bahama Lug Chukka Cloth shoe!. ... more

Sperry Top-Sider Men's Bahama Lug Chukka Casual Shoe

Feel secure with every step and stylish all season long when you wear the Sperry Bahama Lug Chukka Cloth shoe!.

Amazon Marketplace

$42.50

go to store
Sperry Top-Sider Men's Billfish Ultralite Chukka Boot

Sperry Top-Sider Men's Billfish Ultralite Chukka Boot

Leather, nubuck, and mesh upper. 360-degree lacing system. EVA midsole. Non-marking rubber outsole. Patent-pending Adaptive Wave-Siping tread ... more

Sperry Top-Sider Men's Billfish Ultralite Chukka Boot

Leather, nubuck, and mesh upper. 360-degree lacing system. EVA midsole. Non-marking rubber outsole. Patent-pending Adaptive Wave-Siping tread

Amazon Marketplace

$119.95

go to store
Sperry Top-Sider Men's Dockyard Ox Chukka Boot

Sperry Top-Sider Men's Dockyard Ox Chukka Boot

Style chukka ... more

$209.99

go to store
Sperry Top-Sider Men's A/O Lug Chukka Boot

Sperry Top-Sider Men's A/O Lug Chukka Boot

Great for every-day use, the new Sperry Top-Sider A/O Lug Chukka is a rugged, lugged nautical casual shoe ideal for autumn. Crafted with genuine hand-sewn waterproof leather with true moccassin construction to ensure longevity of wear. This incredible... ... more

Sperry Top-Sider Men's A/O Lug Chukka Boot

Great for every-day use, the new Sperry Top-Sider A/O Lug Chukka is a rugged, lugged nautical casual shoe ideal for autumn. Crafted with genuine hand-sewn waterproof leather with true moccassin construction to ensure longevity of wear. This incredible...

Amazon.com

$73.77

go to store
Sperry Top-Sider Men's AO Cyclone Chukka Boot

Sperry Top-Sider Men's AO Cyclone Chukka Boot

Boat shoe-inspired chukka boot featuring moccasin toe and rawhide lacing ... more

Sperry Top-Sider Men's AO Cyclone Chukka Boot

Boat shoe-inspired chukka boot featuring moccasin toe and rawhide lacing

Amazon Marketplace

$99.95

go to store
Sperry Top-Sider Men's Boatyard Chukka Winter Boot

Sperry Top-Sider Men's Boatyard Chukka Winter Boot

Boat deck chukka ... more

$109.90

go to store
Sperry Top-Sider Men's Boat Duck-Cloth Chukka Boot

Sperry Top-Sider Men's Boat Duck-Cloth Chukka Boot

Casual fall boat ... more

$66.54

go to store
Sperry Top-Sider Men's Winter Chukka Boot

Sperry Top-Sider Men's Winter Chukka Boot

Casual fall boat ... more

$119.99

go to store
Sperry Top-Sider Men's Gold Chukka Boot

Sperry Top-Sider Men's Gold Chukka Boot

Sperry Top-Sider Men's Gold Chukka Boot ... more

Sperry Top-Sider Men's Gold Chukka Boot

Sperry Top-Sider Men's Gold Chukka Boot

Amazon.com

$160.95

go to store
Sperry Top-Sider Men's Dockyard Alpine Chukka Boot

Sperry Top-Sider Men's Dockyard Alpine Chukka Boot

Chukka boot ... more

$53.86

go to store
Sperry Top-Sider Men's Boat Plaid Chukka Boot

Sperry Top-Sider Men's Boat Plaid Chukka Boot

boat shoe ... more

$140.00

go to store
Sperry Top-Sider Men's Dockyard Chukka Boot

Sperry Top-Sider Men's Dockyard Chukka Boot

Fashion work chukka boot ... more

$41.96

go to store
Sperry Top-Sider Men's Dockyard Chukka Boot

Sperry Top-Sider Men's Dockyard Chukka Boot

Chukka boot ... more

$44.34

go to store
Sperry Top-Sider Men's Bahama Boot

Sperry Top-Sider Men's Bahama Boot

Rustproof eyelets with frontal laces for an adjustable, secure fit. Rubber outsole for ultimate wet and dry traction. Fabric lining and insole. Imported. ... more

Sperry Top-Sider Men's Bahama Boot

Rustproof eyelets with frontal laces for an adjustable, secure fit. Rubber outsole for ultimate wet and dry traction. Fabric lining and insole. Imported.

Amazon.com

$44.99

go to store
Sperry Top-Sider Men's Sojourn Duck Boot

Sperry Top-Sider Men's Sojourn Duck Boot

Travel to far reaches with confidence in the Sojourn Duck Chukka boot.. ... more

Sperry Top-Sider Men's Sojourn Duck Boot

Travel to far reaches with confidence in the Sojourn Duck Chukka boot..

Amazon.com

$98.96

go to store
Sperry Top-Sider Gold Norfolk ASV Chukka - Men's

Sperry Top-Sider Gold Norfolk ASV Chukka - Men's

The Sperry Men's Gold Norfolk ASV Chukka combines the classic look of an oxford with a chukka silhouette for understated sophistication that can be classed up with a summer suit or dressed down with jeans and a T-shirt. Of course, comfort counts just... ... more

Sperry Top-Sider Gold Norfolk ASV Chukka - Men's

The Sperry Men's Gold Norfolk ASV Chukka combines the classic look of an oxford with a chukka silhouette for understated sophistication that can be classed up with a summer suit or dressed down with jeans and a T-shirt. Of course, comfort counts just...

Amazon.com

$149.97

FREE shipping

go to store
Sperry Top-Sider Men's Grey Wool CVO Sneaker

Sperry Top-Sider Men's Grey Wool CVO Sneaker

Vulcanized construction ensures a secure bond between upper and outsole. Experience the comfort of water resistant wool. Non-marking rubber outsole with razor cut Wave-SipingTM ensures ultimate wet/dry traction. This iconic style is an eye-catching... ... more

Sperry Top-Sider Men's Grey Wool CVO Sneaker

Vulcanized construction ensures a secure bond between upper and outsole. Experience the comfort of water resistant wool. Non-marking rubber outsole with razor cut Wave-SipingTM ensures ultimate wet/dry traction. This iconic style is an eye-catching...

Amazon.com

$42.19

FREE shipping

go to store
Sperry Top-Sider Men's Avenue Duck Boot Chukka Boot

Sperry Top-Sider Men's Avenue Duck Boot Chukka Boot

Duck lace boot ... more

$78.00

FREE shipping

go to store