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Purchase two select styles for the price of $99 with code 2FORYOU at checkout. Offer valid through May 22nd, 2022 at 11:59 PM ET. While supplies last. Offer does not apply on previous purchases, and cannot be combined with other offers. Offer applies to US orders only. Some restrictions may apply.

Purchase two select styles for the price of $99 with code 2FORYOU at checkout. Offer valid through May 22nd, 2022 at 11:59 PM ET. While supplies last. Offer does not apply on previous purchases, and cannot be combined with other offers. Offer applies to US orders only. Some restrictions may apply.

this weekend only!

2 for $99

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Get a free sneaker cleaner with any sneaker purchase with code CLEANSNEAKS at checkout. Offer expires June 30th, 2022 at 11:59PM PT. While supplies last. Excludes kids styles. Not valid on prior purchases. Offer valid only on Sperry.com. Valid on US orders only. Some restrictions may apply.

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Free express shipping on full price Gold Cup styles. Offer automatically applied at checkout.

Gold Cup shoes in a variety of colors on slate and moss.

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Get 20% off your next purchase when you refer a friend to Sperry.com. Your friend will receive 20% off their purchase of $75+ at Sperry.com. Please read all terms and conditions. Offer valid on US orders only. Some restrictions may apply.

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The Gold Cup Collection

Delivering superior craftsmanship,
comfort, and style.

  1. Home
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Men's Gold Cup Shoes 68 Products

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68 Products

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  • Boat Shoes (38)
  • Boots (5)
  • Chukkas (3)
  • Lace Ups (7)
  • Loafers (10)
  • Oxfords (3)
  • Slip Ons (2)
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Material
  • Leather (31)
  • Nubuck (7)
  • Suede (17)
Price
  • $50 - $75 (1)
  • $75 - $100 (2)
  • $100 & Up (65)
Collection
  • Authentic Original (20)
  • Gold Cup (36)

Featured Gold Cup Luxury

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

    Men's Gold Cup Authentic Original Glove Leather Boat Shoe

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    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

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Brown
    Navy
    Tan
  • Gold Cup Authentic Original Glove Leather Boat Shoe, Navy, dynamic

    Men's Gold Cup Authentic Original Glove Leather Boat Shoe

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Brown
    Navy
    Tan
  • Sunspel x Sperry Authentic Original 2-Eye Suede Boat Shoe, Navy, dynamic

    Men's Sunspel x Sperry Authentic Original 2-Eye Suede Boat Shoe

    Sale Price $375.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Ameretto
    Navy
    Tan
  • Sunspel x Sperry Authentic Original 2-Eye Suede Boat Shoe, Tan, dynamic

    Men's Sunspel x Sperry Authentic Original 2-Eye Suede Boat Shoe

    Sale Price $375.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Ameretto
    Navy
    Tan
  • Sperry x Sunspel. Handcrafted in Maine with impeccable details for a unique, one-of-a-kind experience.
  • Sunspel x Sperry Authentic Original 2-Eye Suede Boat Shoe, Ameretto, dynamic

    Men's Sunspel x Sperry Authentic Original 2-Eye Suede Boat Shoe

    Sale Price $375.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Ameretto
    Navy
    Tan
  • Gold Cup Authentic Original 2-Eye Cross Lace Nubuck Boat Shoe, Cream, dynamic

    Men's Gold Cup Authentic Original 2-Eye Cross Lace Nubuck Boat Shoe

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Blue
    Cream
    Green
  • Gold Cup Authentic Original 2-Eye Cross Lace Nubuck Boat Shoe, Blue, dynamic

    Men's Gold Cup Authentic Original 2-Eye Cross Lace Nubuck Boat Shoe

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Blue
    Cream
    Green
  • Gold Cup Authentic Original 2-Eye Cross Lace Nubuck Boat Shoe, Green, dynamic

    Men's Gold Cup Authentic Original 2-Eye Cross Lace Nubuck Boat Shoe

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Blue
    Cream
    Green
  • Gold Cup Authentic Original Boat Shoe, Brown, dynamic

    Men's Gold Cup Authentic Original Boat Shoe

    Sale Price $164.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Brown
    Navy
    Tan
  • Gold Cup Authentic Original Boat Shoe, Tan, dynamic

    Men's Gold Cup Authentic Original Boat Shoe

    Sale Price $164.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Brown
    Navy
    Tan
  • Gold Cup Authentic Original Boat Shoe, Navy, dynamic

    Men's Gold Cup Authentic Original Boat Shoe

    Sale Price $164.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Brown
    Navy
    Tan
  • Gold Cup Authentic Original Suede Boat Shoe, Tan, dynamic

    Men's Gold Cup Authentic Original Suede Boat Shoe

    Sale Price $164.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Navy
    Olive
    Tan
  • Gold Cup Authentic Original Suede Boat Shoe, Olive, dynamic

    Men's Gold Cup Authentic Original Suede Boat Shoe

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Navy
    Olive
    Tan
  • Gold Cup Authentic Original Suede Boat Shoe, Navy, dynamic

    Men's Gold Cup Authentic Original Suede Boat Shoe

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Navy
    Olive
    Tan
  • Gold Cup Authentic Original Rivingston Boat Shoe, Navy, dynamic

    Men's Gold Cup Authentic Original Rivingston Boat Shoe

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Grey
    Navy
  • Gold Cup Authentic Original Rivingston Boat Shoe, Grey, dynamic

    Men's Gold Cup Authentic Original Rivingston Boat Shoe

    Sale Price $159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Grey
    Navy
  • Gold Cup Striper PLUSHWAVE CVO Sneaker, Soft Tan, dynamic

    Men's Gold Cup Striper PLUSHWAVE CVO Sneaker

    Sale Price $139.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Soft Tan
    White
  • Gold Cup Striper PLUSHWAVE CVO Sneaker, White, dynamic

    Men's Gold Cup Striper PLUSHWAVE CVO Sneaker

    Sale Price $139.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Soft Tan
    White
  • Gold Cup Cabo PLUSHWAVE Penny Loafer, Tan, dynamic

    Men's Gold Cup Cabo PLUSHWAVE Penny Loafer

    Sale Price$143.96 Regular Price$159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Navy
    Tan
  • Gold Cup Cabo PLUSHWAVE Penny Loafer, Navy, dynamic

    Men's Gold Cup Cabo PLUSHWAVE Penny Loafer

    Sale Price$143.96 Regular Price$159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Navy
    Tan
  • Gold Cup Cabo PLUSHWAVE 4-Eye Oxford, Tan Suede, dynamic

    Men's Gold Cup Cabo PLUSHWAVE 4-Eye Oxford

    Sale Price$143.96 Regular Price$159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Grey Suede
    Sand Suede
    Tan Suede
  • Gold Cup Cabo PLUSHWAVE 4-Eye Oxford, Grey Suede, dynamic

    Men's Gold Cup Cabo PLUSHWAVE 4-Eye Oxford

    Sale Price$143.96 Regular Price$159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Grey Suede
    Sand Suede
    Tan Suede
  • Gold Cup Cabo PLUSHWAVE 4-Eye Oxford, Sand Suede, dynamic

    Men's Gold Cup Cabo PLUSHWAVE 4-Eye Oxford

    Sale Price$143.96 Regular Price$159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Grey Suede
    Sand Suede
    Tan Suede
  • Gold Cup Cabo PLUSHWAVE Slip On Loafer, Blue Nubuck, dynamic

    Men's Gold Cup Cabo PLUSHWAVE Slip On Loafer

    Sale Price$143.96 Regular Price$159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Blue Nubuck
    Bone Nubuck
  • Gold Cup Cabo PLUSHWAVE Slip On Loafer, Bone Nubuck, dynamic

    Men's Gold Cup Cabo PLUSHWAVE Slip On Loafer

    Sale Price$143.96 Regular Price$159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Blue Nubuck
    Bone Nubuck
  • Gold Cup Meridian Driver, Tan, dynamic

    Men's Gold Cup Meridian Driver

    Sale Price $179.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    Tan
  • Gold Cup Meridian Driver, Black, dynamic

    Men's Gold Cup Meridian Driver

    Sale Price $179.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    Tan
  • Gold Cup Harpswell 1-Eye Driver, Tan, dynamic

    Men's Gold Cup Harpswell 1-Eye Driver

    Sale Price $164.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
  • Sperry x John Legend Signature PLUSHWAVE Boat Shoe, Sand, dynamic

    Men's Sperry x John Legend Signature PLUSHWAVE Boat Shoe

    Sale Price$101.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    8 Colors
    Air Force Blue
    Cream
    Gunmetal
    Lilac
    Navy
    Rust
    Salmon
    Sand
  • Sperry x John Legend Signature PLUSHWAVE Boat Shoe, Cream, dynamic

    Men's Sperry x John Legend Signature PLUSHWAVE Boat Shoe

    Sale Price$101.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    8 Colors
    Air Force Blue
    Cream
    Gunmetal
    Lilac
    Navy
    Rust
    Salmon
    Sand
  • Sperry x John Legend Signature PLUSHWAVE Boat Shoe, Air Force Blue, dynamic

    Men's Sperry x John Legend Signature PLUSHWAVE Boat Shoe

    Sale Price$101.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    8 Colors
    Air Force Blue
    Cream
    Gunmetal
    Lilac
    Navy
    Rust
    Salmon
    Sand
  • Sperry x John Legend Signature PLUSHWAVE Boat Shoe, Gunmetal, dynamic

    Men's Sperry x John Legend Signature PLUSHWAVE Boat Shoe

    Sale Price$101.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    8 Colors
    Air Force Blue
    Cream
    Gunmetal
    Lilac
    Navy
    Rust
    Salmon
    Sand
  • Sperry x John Legend Signature PLUSHWAVE Boat Shoe, Navy, dynamic

    Men's Sperry x John Legend Signature PLUSHWAVE Boat Shoe

    Sale Price$101.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    8 Colors
    Air Force Blue
    Cream
    Gunmetal
    Lilac
    Navy
    Rust
    Salmon
    Sand
  • Sperry x John Legend Signature PLUSHWAVE Boat Shoe, Lilac, dynamic

    Men's Sperry x John Legend Signature PLUSHWAVE Boat Shoe

    Sale Price$101.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    8 Colors
    Air Force Blue
    Cream
    Gunmetal
    Lilac
    Navy
    Rust
    Salmon
    Sand
  • Sperry x John Legend Signature PLUSHWAVE Boat Shoe, Salmon, dynamic

    Men's Sperry x John Legend Signature PLUSHWAVE Boat Shoe

    Sale Price$101.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    8 Colors
    Air Force Blue
    Cream
    Gunmetal
    Lilac
    Navy
    Rust
    Salmon
    Sand
  • Sperry x John Legend Signature PLUSHWAVE Boat Shoe, Rust, dynamic

    Men's Sperry x John Legend Signature PLUSHWAVE Boat Shoe

    Sale Price$101.96 Regular Price$119.95
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    Free Gold Cup Shoe Care Kit with Purchase
    8 Colors
    Air Force Blue
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    Lilac
    Navy
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  • Gold Cup Davenport Driver, Tan, dynamic

    Men's Gold Cup Davenport Driver

    Sale Price $164.95
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    Free Gold Cup Shoe Care Kit with Purchase
  • Gold Cup Handcrafted in Maine Authentic Original Boat Shoe, Natural, dynamic

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

    Sale Price $374.95
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    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

    Sale Price $374.95
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    3 Colors
    Brown
    Navy
    Natural
  • Gold Cup Handcrafted in Maine Authentic Original Boat Shoe, Brown, dynamic

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

    Sale Price $374.95
    Wishlist Added to Wishlist
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    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

    Sale Price $374.95
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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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