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sperry chukka

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$65.00 and Below(32)

$65.01 - $80.00(29)

$80.01 - $95.00(41)

$95.01 - $100.00(24)

$100.01 and Above(17)

Sperry Top-Sider Men's Bahama Chukka

$44.00

$4.84

Cashback

Endless.com

Sperry Top-Sider Men's Bahama Chukka

0 reviews

$44.00

$4.84

Cashback

Buy Sperry Top-Sider Men's Bahama Chukka from Endless.com! The Bahama chukka raises the original Sperry Top-Sider boat shoe to a higher profile. Featuring a touchably soft and smooth leather upper, contrasting stitching accents, and a moc-style toe,...

Endless.com

Sperry Top-Sider Men's Halyard Chukka Boot - Brown

$39.94

$0.80

Cashback

DSW

Sperry Top-Sider Men's Halyard Chukka Boot - Brown

0 reviews

$39.94

$0.80

Cashback

DSW

Sperry Top-Sider Men's Seamate Chukka Sneaker

$35.00

$3.85

Cashback

Endless.com

Sperry Top-Sider Men's Seamate Chukka Sneaker

0 reviews

$35.00

$3.85

Cashback

Buy Sperry Top-Sider Men's Seamate Chukka Sneaker from Endless.com! Best known for boat shoes that have logged more miles of open ocean than any other brand, the Sperry Top-Sider story began on a raw winter day in New England. When avid sailor and...

Endless.com

Sperry Top-Sider Men's Bahama Chukka Fashion Sneaker

$35.00

$3.85

Cashback

Endless.com

Sperry Top-Sider Men's Bahama Chukka Fashion Sneaker

0 reviews

$35.00

$3.85

Cashback

Buy Sperry Top-Sider Men's Bahama Chukka Fashion Sneaker from Endless.com! Best known for boat shoes that have logged more miles of open ocean than any other brand, the Sperry Top-Sider story began on a raw winter day in New England. When avid sailor...

Endless.com

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

$65.00

$7.15

Cashback

Endless.com

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

0 reviews

$65.00

$7.15

Cashback

Buy Sperry Top-Sider Men's A/O Wool Chukka Boot from Endless.com! Sperry Top-Sider Men's A/O Wool Chukka Boot

Endless.com

Sperry Top-Sider Men's Shipyard Lonshreman Chukka...

$96.00

$10.56

Cashback

Endless.com

Sperry Top-Sider Men's Shipyard Lonshreman Chukka Boot

0 reviews

$96.00

$10.56

Cashback

Buy Sperry Top-Sider Men's Shipyard Lonshreman Chukka Boot from Endless.com! Sperry Top-Sider Men's Shipyard Lonshreman Chukka Boot

Endless.com

Sperry Top-Sider Men's a/o Chukka Boat Shoe

$85.00

$9.35

Cashback

Endless.com

Sperry Top-Sider Men's a/o Chukka Boat Shoe

0 reviews

$85.00

$9.35

Cashback

Buy Sperry Top-Sider Men's a/o Chukka Boat Shoe from Endless.com! Sperry Top-Sider Men's a/o Chukka Boat Shoe

Endless.com

Sperry Top-Sider Men's a/o Chukka Boat Shoe

$47.50

$5.23

Cashback

Endless.com

Sperry Top-Sider Men's a/o Chukka Boat Shoe

0 reviews

$47.50

$5.23

Cashback

Buy Sperry Top-Sider Men's a/o Chukka Boat Shoe from Endless.com! Guys, upgrade your outdoorsy wear and blend sophistication with sporty style in this suede lace-up from Sperry Top-Sider. Featuring genuine handsewn construction, the a/o Chukka Boat...

Endless.com

Sperry Top-Sider Men's Boat Lug Chukka Boot

$65.00

$7.15

Cashback

Endless.com

Sperry Top-Sider Men's Boat Lug Chukka Boot

0 reviews

$65.00

$7.15

Cashback

Buy Sperry Top-Sider Men's Boat Lug Chukka Boot from Endless.com! Classic dockside details and a thick, urban sole make the Boat Lug from Sperry Top-Sider a fresh take on a classic. Contrast mocc stitching and 360 degree laces deliver timeless charm...

Endless.com

Sperry Top-Sider Bahama Chukka Suede Black Suede

$80.00Sale $64.00

$7.04

Cashback

Planet Shoes

Sperry Top-Sider Bahama Chukka Suede Black Suede

0 reviews

$80.00Sale $64.00

$7.04

Cashback

Flaunt a modern twist on a classic favorite with the Sperry Top-Sider Bahama Chukka Suede. Made with the same comfort and protection you love from the original, this men's chukka has a secure fit, 360-degree lacing system and handsewn Tru-Moc...

Planet Shoes

Sperry Top-Sider Men's Seamate Chukka Burnished F...

$41.13

$4.52

Cashback

Endless.com

Sperry Top-Sider Men's Seamate Chukka Burnished Fashion Sneaker

0 reviews

$41.13

$4.52

Cashback

Buy Sperry Top-Sider Men's Seamate Chukka Burnished Fashion Sneaker from Endless.com! Sperry Top-Sider Men's Seamate Chukka Burnished Fashion Sneaker

Endless.com

Sperry Top-Sider Harbor Cup Chukka Dark Brown

$100.00Sale $79.00

$8.69

Cashback

Planet Shoes

Sperry Top-Sider Harbor Cup Chukka Dark Brown

0 reviews

$100.00Sale $79.00

$8.69

Cashback

The original Sperry silhouette adapted for a more urban feel, the Sperry Chukkas are made to appease the trendy and style savvy guy. The genuine handsewn construction makes for the ultimate in simple styling. Slip on a pair of these Sperry Top-Sider...

Planet Shoes

Sperry Top-Sider Harbor Cup Chukka Dark Tan

$100.00Sale $79.00

$8.69

Cashback

Planet Shoes

Sperry Top-Sider Harbor Cup Chukka Dark Tan

0 reviews

$100.00Sale $79.00

$8.69

Cashback

Planet Shoes

Sperry Top-Sider A/O Chukka Boot (Toddler/Little ...

$44.00

$4.84

Cashback

Endless.com

Sperry Top-Sider A/O Chukka Boot (Toddler/Little Kid/Big Kid)

0 reviews

$44.00

$4.84

Cashback

Buy Sperry Top-Sider A/O Chukka Boot (Toddler/Little Kid/Big Kid) from Endless.com! Perfect for that annual family reunion, the Sperry Top-Sider A/O Chukka boot lets him look nice without sacrificing comfort. Composed form a Nubuck upper, this boot...

Endless.com

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

$29.72

$3.27

Cashback

Endless.com

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

0 reviews

$29.72

$3.27

Cashback

Buy Sperry Top-Sider Men's A/O Salt Wash Chukka Boot from Endless.com! Best known for boat shoes that have logged more miles of open ocean than any other brand, the Sperry Top-Sider story began on a raw winter day in New England. When avid sailor and...

Endless.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Gray, 10.5

0 reviews

$99.95

$4.00

Cashback

Featuring a rugged, outdoorsy look and a plush suede upper, the Sperry Top-Sider Harbor Cup Chukka Shoe has the style to carry that Labor-Day-weekend feeling straight on through the rest of fall. Whether you're rubbing a fresh coat of wax into your...

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Brown, 11.0

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Brown, 9.5

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Brown, 13.0

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Gray, 8.0

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Gray, 13.0

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Brown, 8.5

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Gray, 11.0

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Brown, 8.0

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Brown, 10.5

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Brown, 10.0

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Gray, 8.5

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Gray, 10.0

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Gray, 11.5

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's D...

$99.95

$4.00

Cashback

Backcountry.com

Sperry Top-Sider Harbor Cup Chukka Shoe - Men's Dark Gray, 9.0

0 reviews

$99.95

$4.00

Cashback

Backcountry.com

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sperry chukka