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Women's Angelfish Boat Shoe
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Top Results
Women's Angelfish Boat Shoe
$79.95 $89.95
Men's Authentic Original Leather Boat Shoe
$94.95
Women's Crest Vibe Sneaker
$59.95
Women's Saltwater Duck Boot
$99.95 $129.95
Women's Saltwater Tall Cozy Leather Duck Boot
$95.97 $159.95
Women's Authentic Original Boat Shoe
$94.95
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Top Results
Women's Angelfish Boat Shoe
$79.95 $89.95
Men's Authentic Original Leather Boat Shoe
$94.95
Women's Crest Vibe Sneaker
$59.95
Women's Saltwater Duck Boot
$99.95 $129.95
Women's Saltwater Tall Cozy Leather Duck Boot
$95.97 $159.95
Women's Authentic Original Boat Shoe
$94.95
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Men's Gold Cup Shoes

56 Products

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56 Products

Size/Width

Size

  • 7
  • 7.5
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  • 8.5
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  • 10.5
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  • 11.5
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  • Boat Shoes
  • Chukkas
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Material
  • Leather
  • Nubuck
Price
  • $75 - $100
  • $100 & Up
Collection
  • Authentic Original
  • Gold Cup

Featured Gold Cup

 
  • Gold Cup Authentic Original Glove Leather Boat Shoe, Navy, dynamic

    Men's Gold Cup Authentic Original Glove Leather Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Brown
    Navy
    Tan
  • Gold Cup Authentic Original Glove Leather Boat Shoe, Brown, dynamic

    Men's Gold Cup Authentic Original Glove Leather Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Brown
    Navy
    Tan
  • Gold Cup Authentic Original Glove Leather Boat Shoe, Tan, dynamic

    Men's Gold Cup Authentic Original Glove Leather Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Brown
    Navy
    Tan
  • Premium, full-grain leathers in a hand-sewn moccasin construction.
  • Gold Cup Authentic Original Orleans Boat Shoe, Tan, dynamic

    Men's Gold Cup Authentic Original Orleans Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    4 Colors
    Amaretto
    Black
    Grey
    Tan
  • Gold Cup Authentic Original Orleans Boat Shoe, Black, dynamic

    Men's Gold Cup Authentic Original Orleans Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    4 Colors
    Amaretto
    Black
    Grey
    Tan
  • Gold Cup Authentic Original Orleans Boat Shoe, Amaretto, dynamic

    Men's Gold Cup Authentic Original Orleans Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    4 Colors
    Amaretto
    Black
    Grey
    Tan
  • Gold Cup Authentic Original Orleans Boat Shoe, Grey, dynamic

    Men's Gold Cup Authentic Original Orleans Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    4 Colors
    Amaretto
    Black
    Grey
    Tan
  • Gold Cup Authentic Original 2-Eye Burnished Leather Boat Shoe, Grey/Navy, dynamic

    Men's Gold Cup Authentic Original 2-Eye Burnished Leather Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
  • Gold Cup Harpswell 1-Eye Driver, Tan, dynamic

    Men's Gold Cup Harpswell 1-Eye Driver

    $164.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
  • Gold Cup Authentic Original Boat Shoe, Tan, dynamic

    Men's Gold Cup Authentic Original Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Brown
    Navy
    Tan
  • Premium leather uppers and soft lambskin linings that wear better over time.
  • Gold Cup Authentic Original Boat Shoe, Brown, dynamic

    Men's Gold Cup Authentic Original Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Brown
    Navy
    Tan
  • Gold Cup Authentic Original Boat Shoe, Navy, dynamic

    Men's Gold Cup Authentic Original Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Brown
    Navy
    Tan
  • Gold Cup Authentic Original Seaside Boat Shoe, Twig, dynamic

    Men's Gold Cup Authentic Original Seaside Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Lanyard
    Stern
    Twig
  • Anti-Shock and Vibration (ASV) technology reduces the effects of shock by up to 30%.
  • Gold Cup Authentic Original Seaside Boat Shoe, Stern, dynamic

    Men's Gold Cup Authentic Original Seaside Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Lanyard
    Stern
    Twig
  • Gold Cup Authentic Original Seaside Boat Shoe, Lanyard, dynamic

    Men's Gold Cup Authentic Original Seaside Boat Shoe

    $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Lanyard
    Stern
    Twig
  • Gold Cup Harpswell Penny Loafer, Leather Tan, dynamic

    Men's Gold Cup Harpswell Penny Loafer

    $164.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
  • Gold Cup Harpswell Driver, Tan, dynamic

    Men's Gold Cup Harpswell Driver

    $164.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
  • Lambskin linings and Ortholite® insert provide all-day comfort
  • Gold Cup Authentic Original Chukka, Tan, dynamic

    Men's Gold Cup Authentic Original Chukka

    $110.97 $184.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    3 Colors
    Amaretto
    Black
    Tan
  • Gold Cup Authentic Original Chukka, Amaretto, dynamic

    Men's Gold Cup Authentic Original Chukka

    $110.97 $184.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    3 Colors
    Amaretto
    Black
    Tan
  • Gold Cup Authentic Original Chukka, Black, dynamic

    Men's Gold Cup Authentic Original Chukka

    $110.97 $184.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    3 Colors
    Amaretto
    Black
    Tan
  • Rubber heel and full rubber non-marking outsole.
  • Gold Cup Richfield PLUSHWAVE Sneaker, Tan, dynamic

    Men's Gold Cup Richfield PLUSHWAVE Sneaker

    $92.99 $154.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    3 Colors
    Amaretto
    Grey
    Tan
  • Gold Cup Richfield PLUSHWAVE Sneaker, Amaretto, dynamic

    Men's Gold Cup Richfield PLUSHWAVE Sneaker

    $92.99 $154.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    3 Colors
    Amaretto
    Grey
    Tan
  • Gold Cup Richfield PLUSHWAVE Sneaker, Grey, dynamic

    Men's Gold Cup Richfield PLUSHWAVE Sneaker

    $92.99 $154.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    3 Colors
    Amaretto
    Grey
    Tan
  • Gold Cup Handcrafted in Maine Authentic Original Boat Shoe, Brown, dynamic

    Men's Gold Cup Handcrafted in Maine Authentic Original Boat Shoe

    $374.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Brown
    Navy
    Natural
  • Signature Sperry rawhide laces feature our 360 degree Lacing System for a customized fit.
  • Gold Cup Handcrafted in Maine Authentic Original Boat Shoe, Natural, dynamic

    Men's Gold Cup Handcrafted in Maine Authentic Original Boat Shoe

    $374.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Brown
    Navy
    Natural
  • Gold Cup Handcrafted in Maine Authentic Original Boat Shoe, Navy, dynamic

    Men's Gold Cup Handcrafted in Maine Authentic Original Boat Shoe

    $374.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Brown
    Navy
    Natural
  • Gold Cup Handcrafted in Maine Authentic Original Tri-Tone Boat Shoe, Navy/Red/Ivory, dynamic

    Men's Gold Cup Handcrafted in Maine Authentic Original Tri-Tone Boat Shoe

    $374.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    2 Colors
    Navy/Burgundy/Olive
    Navy/Red/Ivory
  • Gold Cup Handcrafted in Maine Authentic Original Tri-Tone Boat Shoe, Navy/Burgundy/Olive, dynamic

    Men's Gold Cup Handcrafted in Maine Authentic Original Tri-Tone Boat Shoe

    $374.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    2 Colors
    Navy/Burgundy/Olive
    Navy/Red/Ivory
  • Gold Cup Handcrafted in Maine 1-Eye Driver, Brown, dynamic

    Men's Gold Cup Handcrafted in Maine 1-Eye Driver

    $374.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
  • Gold Cup Handcrafted in Maine 1-Eye Driver, Tan, dynamic

    Men's Gold Cup Handcrafted in Maine 1-Eye Driver

    $374.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    3 Colors
    Ivory/Tan
    Navy/Tan
    Tan
  • Gold Cup Handcrafted in Maine 1-Eye Driver, Ivory/Tan, dynamic

    Men's Gold Cup Handcrafted in Maine 1-Eye Driver

    $374.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    3 Colors
    Ivory/Tan
    Navy/Tan
    Tan
  • Gold Cup Handcrafted in Maine 1-Eye Driver, Navy/Tan, dynamic

    Men's Gold Cup Handcrafted in Maine 1-Eye Driver

    $374.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    3 Colors
    Ivory/Tan
    Navy/Tan
    Tan
  • Gold Cup Handcrafted in Maine Penny Loafer, Brown, dynamic

    Men's Gold Cup Handcrafted in Maine Penny Loafer

    $374.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    2 Colors
    Brown
    Navy/Brown
  • Gold Cup Handcrafted in Maine Penny Loafer, Navy/Brown, dynamic

    Men's Gold Cup Handcrafted in Maine Penny Loafer

    $374.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    2 Colors
    Brown
    Navy/Brown
  • Gold Cup Exeter Penny Loafer, Black, dynamic

    Men's Gold Cup Exeter Penny Loafer

    $136.99 $179.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
  • Gold Cup Authentic Original Lug Chukka, Tan, dynamic

    Men's Gold Cup Authentic Original Lug Chukka

    $128.99 $184.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
  • Gold Cup ASV 2-Eye Boat Shoe, Amaretto Leather, dynamic

    Men's Gold Cup ASV 2-Eye Boat Shoe

    $179.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
  • Gold Cup Authentic Original Cross Lace Boat Shoe, Ivory/Tan, dynamic

    Men's Gold Cup Authentic Original Cross Lace Boat Shoe

    $95.97 $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Blue/Tan
    Grey/Light Grey
    Ivory/Tan
  • Gold Cup Authentic Original Cross Lace Boat Shoe, Blue/Tan, dynamic

    Men's Gold Cup Authentic Original Cross Lace Boat Shoe

    $95.97 $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Blue/Tan
    Grey/Light Grey
    Ivory/Tan
  • Gold Cup Authentic Original Cross Lace Boat Shoe, Grey/Light Grey, dynamic

    Men's Gold Cup Authentic Original Cross Lace Boat Shoe

    $95.97 $159.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
    3 Colors
    Blue/Tan
    Grey/Light Grey
    Ivory/Tan
  • Gold Cup Boat Shoe w/ ASV, Cymbal, dynamic

    Men's Gold Cup Boat Shoe w/ ASV

    $179.95
    Add to Favorites
    $5 Sock Liner With Code BOATSOCK
  • Gold Cup Handcrafted in Maine Penny Loafer, Tan, dynamic

    Men's Gold Cup Handcrafted in Maine Penny Loafer

    $374.95
    Add to Favorites
    Free Express Shipping on Gold Cup Styles
    2 Colors
    Black
    Tan

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56 Products

Size/Width

Size

  • 7
  • 7.5
  • 8
  • 8.5
  • 9
  • 9.5
  • 10
  • 10.5
  • 11
  • 11.5
  • 12
  • 13
  • 14
  • 15

Width

  • Medium
  • Wide
Color
  • Black
  • Blue
  • Brown
  • Green
  • Grey
  • Red
  • Tan
  • White
Style
  • Boat Shoes
  • Chukkas
  • Lace Ups
  • Loafers
  • Oxfords
  • Slip Ons
+ Show More - Show Less
Material
  • Leather
  • Nubuck
Price
  • $75 - $100
  • $100 & Up
Collection
  • Authentic Original
  • Gold Cup

Recommended Products

Men's Sperry Gold Cup

Dress the part when you seek out epic experiences with the iconic quality, craftsmanship, and style of Sperry Gold Cup Collection shoes for men. The Gold Cup Collection offers iconic Sperry leather shoe styles—including Authentic Original boat shoes, boots, loafers, chukkas, duck boots, and sneakers—interpreted to create an instant effect that communicates understated luxury. Select from an array of Sperry Gold Cup shoes in upscale designs in must-have colors, materials, and finishes; select Sperry Gold Cup shoes also incorporate various other high-end features, like luxurious lambskin lining, high-performance Anti-Shock and Vibration technology, memory foam footbeds, and gold-plated eyelets. From dress shoes to casual shoes, the Sperry Gold Cup Collection has an exceptional shoe to suit your needs in lavish style.

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