Mens Sailing Shoes

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Sperry Top-Sider A/O 2-Eye Neon

Sperry Top-Sider A/O 2-Eye Neon - Black/Neon Yellow Leather (Men's)
 
$89.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Neon

Sperry Top-Sider A/O 2-Eye Neon - Dark Brown/Blue/Blue Leather (Men's)
 
$89.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Neon

Sperry Top-Sider A/O 2-Eye Neon - Grey/Turquoise Leather (Men's)
 
$89.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye Neon

Sperry Top-Sider A/O 2-Eye Neon - Navy/Neon Orange Leather (Men's)
 
$89.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Neon

Sperry Top-Sider A/O 2-Eye Neon - Sahara/Red Leather (Men's)
 
$89.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Neon

Sperry Top-Sider A/O 2-Eye Neon - White/Neon Green Leather (Men's)
 
$89.95 Free Shipping Both Ways!

Sperry Top-Sider Gold Boat ASV

Sperry Top-Sider Gold Boat ASV - Amaretto Leather (Men's)
 
$169.95 Free Shipping Both Ways!
 
Sperry Top-Sider Gold Boat ASV

Sperry Top-Sider Gold Boat ASV - Cognac Leather (Men's)
 
$169.95 Free Shipping Both Ways!
 
Sebago Clovehitch II

Sebago Clovehitch II - Ambergold (Men's)
 
$113.95 Free Shipping Both Ways!

Sebago Clovehitch II

Sebago Clovehitch II - Medium Brown (Men's)
 
$113.95 Free Shipping Both Ways!
 
Sebago Clovehitch II

Sebago Clovehitch II - Walnut Nubuck (Men's)
 
$113.95 Free Shipping Both Ways!
 
Sebago Clovehitch II

Sebago Clovehitch II - Taupe (Men's)
 
$113.95 Free Shipping Both Ways!

Sebago Clovehitch II

Sebago Clovehitch II - Dark Taupe/Dark Brown (Men's)
 
$113.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Burnished

Sperry Top-Sider A/O 2-Eye Burnished - Brown Burnished Leather (Men's)
 
$94.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Burnished

Sperry Top-Sider A/O 2-Eye Burnished - Cool Grey/Cement Burnished Leather (Men's)
 
$94.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye Burnished

Sperry Top-Sider A/O 2-Eye Burnished - Dark Brown/Tan Burnished Leather (Men's)
 
$94.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Burnished

Sperry Top-Sider A/O 2-Eye Burnished - Dark Grey Burnished Leather (Men's)
 
$94.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Burnished

Sperry Top-Sider A/O 2-Eye Burnished - Grey/Yellow Burnished Leather (Men's)
 
$94.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye Burnished

Sperry Top-Sider A/O 2-Eye Burnished - Turquoise/Cool Grey Burnished Leather (Men's)
 
$94.95 Free Shipping Both Ways!
 
Sperry Top-Sider Authentic Original 2-Eye

Sperry Top-Sider Authentic Original 2-Eye - Olive Canvas (Men's)
 
$84.95 Free Shipping Both Ways!
 
Sperry Top-Sider Authentic Original 2-Eye

Sperry Top-Sider Authentic Original 2-Eye - Tan (Men's)
 
$84.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye Canvas

Sperry Top-Sider A/O 2-Eye Canvas - Navy (Men's)
 
$79.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Canvas

Sperry Top-Sider A/O 2-Eye Canvas - Navy/Red/White (Men's)
 
$79.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Canvas

Sperry Top-Sider A/O 2-Eye Canvas - Olive Salt Washed (Men's)
 
$79.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye Canvas

Sperry Top-Sider A/O 2-Eye Canvas - Red (Men's)
 
$79.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Canvas

Sperry Top-Sider A/O 2-Eye Canvas - Red Plaid/Navy (Men's)
 
$79.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Canvas

Sperry Top-Sider A/O 2-Eye Canvas - Taupe (Men's)
 
$79.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye Canvas

Sperry Top-Sider A/O 2-Eye Canvas - Turquoise (Men's)
 
$79.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Perfed Suede

Sperry Top-Sider A/O 2-Eye Perfed Suede - Grey Suede (Men's)
 
$94.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Perfed Suede

Sperry Top-Sider A/O 2-Eye Perfed Suede - Navy Suede (Men's)
 
$94.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye Perfed Suede

Sperry Top-Sider A/O 2-Eye Perfed Suede - Orange Suede (Men's)
 
$94.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Perfed Suede

Sperry Top-Sider A/O 2-Eye Perfed Suede - Tan Suede (Men's)
 
$94.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye White Wash

Sperry Top-Sider A/O 2-Eye White Wash - Dark Blue Leather (Men's)
 
$94.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye White Wash

Sperry Top-Sider A/O 2-Eye White Wash - Dark Red Leather (Men's)
 
$94.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye White Wash

Sperry Top-Sider A/O 2-Eye White Wash - Orange Leather (Men's)
 
$94.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye White Wash

Sperry Top-Sider A/O 2-Eye White Wash - Tan Leather (Men's)
 
$94.95 Free Shipping Both Ways!

Mens Sailing Shoes

1-36 of 156 results   1 2 3 4 5  Next »
Sebago Docksides
Sebago March 16, 2013
Reviewer: Tony from Texas
Not quite the quality I expected but value for the money. Comfortable and fit well.
Wears this shoe: Wear the shoes any time of the day.
Dockers Darwin
Very comfortable March 07, 2013
Reviewer: John from NC
These shoes are very comfortable and look great too!
Wears this shoe: Daily at work
Sperry Top-Sider Sea Kite
So Far So Good February 03, 2013
Reviewer: Tom from Houston, Texas
I was a big fan of the discontinued Sperry/New Balance SB870 and have been looking for a replacement. I'm not a boater but just liked them for their overall comfort as a knock around shoe. Nothing Sperry has offered has come close in my opinion until now with the Sea Kite. I have only had them for a short while so it is a little early to give a definitive thumbs up, but so far they have been very comfortable and hopefully will continue to do so.
Wears this shoe: the last few weeks
Sebago Spinnaker
Nice looking, solidly made boat shoe. January 02, 2013
Reviewer: Oskian from Homestead, Florida
Boat shoes are very popular in the South where I live (Florida). I particularly like Sperry, Sebago & Timberland.These Spinnakers are great lookers, very comfy and durable. When I can I will buy another pair of a different color.Can't go wrong with Sebago!
Wears this shoe: Everywhere
Sebago Spinnaker
Great looking shoe January 01, 2013
Reviewer: D from Galveston, TX
I have liked this style for years and absolutely love the colors used.
Wears this shoe: Work