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2 for $99

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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.

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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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Featured View All

 
  • Authentic Original 2-Eye Tri-Tone Boat Shoe, Navy Multi, dynamic

    Men's Authentic Original 2-Eye Tri-Tone Boat Shoe

    Sale Price$75.96 Regular Price$94.95
    Wishlist Added to Wishlist
    Quick Add
  • Striper II Storm CVO Waterproof Leather Sneaker, Tan Nubuck, dynamic

    Men's Striper II Storm CVO Waterproof Leather Sneaker

    Sale Price$53.97 Regular Price$89.95
    Wishlist Added to Wishlist
    Quick Add
  • 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
  • Authentic Original Playa Boat Shoe, Navy, dynamic

    Men's Authentic Original Playa Boat Shoe

    Sale Price$75.96 Regular Price$94.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Navy
    Taupe
  • 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
  • Outer Banks 2-Eye Suede Boat Shoe, Brown, dynamic

    Men's Outer Banks 2-Eye Suede Boat Shoe

    Sale Price$71.96 Regular Price$79.95
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Brown
    Dark Grey
    Light Grey
    Navy
  • Gold Cup Meridian Croc Embossed Driver, Tan, dynamic

    Men's Gold Cup Meridian Croc Embossed Driver

    Sale Price$143.96 Regular Price$179.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
  • Striper Storm Hiker Boot, Taupe, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price$89.96 Regular Price$99.95
    Wishlist Added to Wishlist
    Quick Add
    6 Colors
    Black
    Black Multi
    Brown/Camo
    Navy
    Tan
    Taupe
  • SeaCycled™ Striper II CVO Sneaker, White, dynamic

    Men's SeaCycled™ Striper II CVO Sneaker

    Sale Price$58.46 Regular Price$64.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Grey
    White
  • 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 Soletide Sneaker, White, dynamic

    Men's Sperry x John Legend Soletide Sneaker

    Sale Price$94.95 Regular Price$99.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    White
  • 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, 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
  • Striper II CVO Baja Linen Sneaker, Light Grey, dynamic

    Men's Striper II CVO Baja Linen Sneaker

    Sale Price$53.96 Regular Price$59.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Light Grey
    Red
    Taupe
  • Sperry x John Legend Soletide Sneaker, Black, dynamic

    Men's Sperry x John Legend Soletide Sneaker

    Sale Price$94.95 Regular Price$99.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    White
  • Gold Cup Authentic Original 2-Eye Croc Embossed Boat Shoe, Navy Multi, dynamic

    Men's Gold Cup Authentic Original 2-Eye Croc Embossed Boat Shoe

    Sale Price$127.96 Regular Price$159.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
  • Striper Storm Hiker Boot, Black, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price$89.96 Regular Price$99.95
    Wishlist Added to Wishlist
    Quick Add
    6 Colors
    Black
    Black Multi
    Brown/Camo
    Navy
    Tan
    Taupe
  • Striper II CVO Baja Linen Sneaker, Taupe, dynamic

    Men's Striper II CVO Baja Linen Sneaker

    Sale Price$53.96 Regular Price$59.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Light Grey
    Red
    Taupe
  • 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
  • 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
  • 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
  • Authentic Original Playa Boat Shoe, Taupe, dynamic

    Men's Authentic Original Playa Boat Shoe

    Sale Price$75.96 Regular Price$94.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Navy
    Taupe
  • Cloud Authentic Original 3-Eye Leather Boat Shoe, Navy, dynamic

    Men's Cloud Authentic Original 3-Eye Leather Boat Shoe

    Sale Price$112.00 Regular Price$140.00
    Wishlist Added to Wishlist
    Quick Add
  • Striper PLUSHWAVE CVO Checkmake Sneaker, Blue, dynamic

    Men's Striper PLUSHWAVE CVO Checkmake Sneaker

    Sale Price$80.96 Regular Price$89.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Blue
    Grey
    Red
  • Striper PLUSHWAVE CVO Checkmake Sneaker, Grey, dynamic

    Men's Striper PLUSHWAVE CVO Checkmake Sneaker

    Sale Price$80.96 Regular Price$89.95
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Blue
    Grey
    Red
  • 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
  • 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
  • Bahama PLUSHWAVE Checkmate Sneaker, White, dynamic

    Men's Bahama PLUSHWAVE Checkmate Sneaker

    Sale Price$80.96 Regular Price$89.95
    Wishlist Added to Wishlist
    Quick Add
  • Authentic Original PLUSHWAVE Lug Chukka, Taupe, dynamic

    Men's Authentic Original PLUSHWAVE Lug Chukka

    Sale Price$116.96 Regular Price$129.95
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Black
    Brown
    Tan
    Taupe
  • Gold Cup Commodore PLUSHWAVE Chukka, Tan, dynamic

    Men's Gold Cup Commodore PLUSHWAVE Chukka

    Sale Price$170.96 Regular Price$189.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    Tan
  • Authentic Original Tumbled Leather Boat Chukka, Tan, dynamic

    Men's Authentic Original Tumbled Leather Boat Chukka

    Sale Price$107.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Dark Brown
    Tan
  • Cold Bay Duck Boot w/ Thinsulate™, Taupe/Navy, dynamic

    Men's Cold Bay Duck Boot w/ Thinsulate™

    Sale Price$107.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Tan/Brown
    Taupe/Navy
  • Bahama II PLUSHWAVE Checkmate Sneaker, Grey, dynamic

    Men's Bahama II PLUSHWAVE Checkmate Sneaker

    Sale Price$71.96 Regular Price$89.95
    Wishlist Added to Wishlist
    Quick Add
  • Gold Cup Commodore PLUSHWAVE Chukka, Black, dynamic

    Men's Gold Cup Commodore PLUSHWAVE Chukka

    Sale Price$170.96 Regular Price$189.95
    Wishlist Added to Wishlist
    Quick Add
    Free Gold Cup Shoe Care Kit with Purchase
    2 Colors
    Black
    Tan
  • Striper II CVO Ombre Sneaker, Vapor, dynamic

    Men's Striper II CVO Ombre Sneaker

    Sale Price$53.96 Regular Price$59.95
    Wishlist Added to Wishlist
    Quick Add
  • Cold Bay Duck Boot w/ Thinsulate™, Navy/Grey, dynamic

    Men's Cold Bay Duck Boot w/ Thinsulate™

    Sale Price$107.96 Regular Price$119.95
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Navy/Grey
  • Sperry x John Legend Commodore PLUSHWAVE Boot, Rust, dynamic

    Men's Sperry x John Legend Commodore PLUSHWAVE Boot

    Sale Price$179.96 Regular Price$199.95
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    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Bone
    Oxblood
    Rust
  • Striper PLUSHWAVE CVO Checkmake Sneaker, Red, dynamic

    Men's Striper PLUSHWAVE CVO Checkmake Sneaker

    Sale Price$80.96 Regular Price$89.95
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    3 Colors
    Blue
    Grey
    Red
  • Moc-Sider Buffalo Check Slip On, Blue Plaid, dynamic

    Men's Moc-Sider Buffalo Check Slip On

    Sale Price$34.99 Regular Price$69.95
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    3 Colors
    Blue Plaid
    Grey Plaid
    Red Plaid
  • Striper Storm Hiker Boot, Navy, dynamic

    Men's Striper Storm Hiker Boot

    Sale Price$89.96 Regular Price$99.95
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    6 Colors
    Black
    Black Multi
    Brown/Camo
    Navy
    Tan
    Taupe
  • Unisex Cloud Linen Slip On Sneaker, Navy, dynamic

    Unisex Cloud Linen Slip On Sneaker

    Sale Price$89.96 Regular Price$99.95
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    2 Colors
    Navy
    Tan
  • Striper II CVO Baja Linen Sneaker, Ivory, dynamic

    Men's Striper II CVO Baja Linen Sneaker

    Sale Price$23.98 Regular Price$59.95
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  • Cold Bay Chukka w/ Thinsulate™, Buffalo Check, dynamic

    Men's Cold Bay Chukka w/ Thinsulate™

    Sale Price$43.98 Regular Price$109.95
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  • Unisex Cloud Captain's Wave Print Oxford, Navy, dynamic

    Unisex Cloud Captain's Wave Print Oxford

    Sale Price$134.96 Regular Price$149.95
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    2 Colors
    Birch
    Navy
  • Cloud CVO Bandana Sneaker, Blue/Red, dynamic

    Men's Cloud CVO Bandana Sneaker

    Sale Price$81.00 Regular Price$90.00
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  • Striper PLUSHWAVE Sneaker, White, dynamic

    Men's Striper PLUSHWAVE Sneaker

    Sale Price$80.96 Regular Price$99.95
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  • 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
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    Free Gold Cup Shoe Care Kit with Purchase
    3 Colors
    Grey Suede
    Sand Suede
    Tan Suede
  • Cloud Authentic Original Tassel Loafer, Veg Natural, dynamic

    Men's Cloud Authentic Original Tassel Loafer

    Sale Price$160.00 Regular Price$200.00
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Build your own sea-inspired style from the ground up with our impressive assortment of adventure-ready and always-comfortable shoes for men. From flip flops to duck boots and everything in between, Sperry men's shoes help you put your best foot forward no matter the occasion. Hit the beach in our men's sandals or flip flops, or hit the deck in our Authentic Original men's boat shoe. Then hit the town in smart casual men's shoes like our Sojourn leather shoe, Gold Cup Kennebunk woven loafer or men's chukka boot, with a variety of colors and detailing options available. If you're looking for the perfect versatile men's shoes for jeans or shorts, our men's sneakers and boat shoes provide sleek styling and flexibility to suit any outfit and durable quality to suit any adventure. Wherever yours takes you, take your boldest steps yet with Sperry.

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