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  • New
    • New Arrivals
      • Shop All Women's
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      • Shop All Kids'
    • Just In
      • Pride Collection
      • Father's Day Gift Guide
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      • Sperry x Yellena James
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      • Platform Shoes
      • Sport
      • Float Slide
    • Shop Now
  • Women
    • Shoes
      • View All
      • Boat Shoes
      • Sandals & Flip flops
      • Sneakers
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      • Wedges & Heels
      • Rain & Duck Boots
      • Boots
      • Slippers
      • Online Exclusives
      • Sale
    • New & Trending
      • New Arrivals
      • Cottage Season
      • Sperry x Yellena James
      • Sperry x Pleasures
      • Platform Shoes
      • Sport
      • Float Slide
      • Best Sellers
    • Collections
      • Authentic Original™
      • Gold Cup™
      • SeaCycled™
      • Pride Collection
      • Gifts for Dad
      • Seaport
      • PLUSHWAVE™
      • Crest Vibe
      • Float
      • Gender Inclusive
      • Cloud
    • Shop Now
  • Men
    • Shoes
      • View All
      • Boat Shoes
      • Sandals
      • Sneakers
      • Loafers & Oxfords
      • Rain & Duck Boots
      • Boots
      • Slippers
      • Online Exclusives
      • Sale
    • New & Trending
      • New Arrivals
      • Cottage Season
      • Sperry x Brooks Brothers
      • Sperry x Pleasures
      • Sperry x Herschel
      • Sport
      • Float Slide
      • Best Sellers
    • Collections
      • Authentic Original™
      • Gold Cup™
      • SeaCycled™
      • Pride Collection
      • Father's Day Gift Guide
      • PLUSHWAVE™
      • Striper II
      • Float
      • Gender Inclusive
      • Cloud
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  1. Home
  2. Date Night

Date Night

49 Products
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Featured Date Night

 
  • Authentic Original™ Boat Shoe, Sahara Leather, dynamic

    Women's Authentic Original™ Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Classic Brown Leather
    Sahara Leather
    Navy
  • Authentic Original™ Boat Shoe, Navy, dynamic

    Women's Authentic Original™ Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Classic Brown Leather
    Sahara Leather
    Navy
  • Authentic Original™ Boat Shoe, Classic Brown Leather, dynamic

    Women's Authentic Original™ Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Classic Brown Leather
    Sahara Leather
    Navy
  • Authentic Original Boat Shoe, Sahara Leather, dynamic

    Men's Authentic Original Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    7 Colors
    Sahara Leather
    Classic Brown
    Tan
    Oatmeal
    Amaretto
    Black
    Brown Buc Brown
  • Authentic Original Boat Shoe, Tan, dynamic

    Men's Authentic Original Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    7 Colors
    Sahara Leather
    Classic Brown
    Tan
    Oatmeal
    Amaretto
    Black
    Brown Buc Brown
  • Authentic Original Boat Shoe, Amaretto, dynamic

    Men's Authentic Original Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    7 Colors
    Sahara Leather
    Classic Brown
    Tan
    Oatmeal
    Amaretto
    Black
    Brown Buc Brown
  • Authentic Original Boat Shoe, Classic Brown, dynamic

    Men's Authentic Original Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    7 Colors
    Sahara Leather
    Classic Brown
    Tan
    Oatmeal
    Amaretto
    Black
    Brown Buc Brown
  • Authentic Original Boat Shoe, Brown Buc Brown, dynamic

    Men's Authentic Original Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    7 Colors
    Sahara Leather
    Classic Brown
    Tan
    Oatmeal
    Amaretto
    Black
    Brown Buc Brown
  • Authentic Original Boat Shoe, Oatmeal, dynamic

    Men's Authentic Original Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    7 Colors
    Sahara Leather
    Classic Brown
    Tan
    Oatmeal
    Amaretto
    Black
    Brown Buc Brown
  • Authentic Original Boat Shoe, Black, dynamic

    Men's Authentic Original Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    7 Colors
    Sahara Leather
    Classic Brown
    Tan
    Oatmeal
    Amaretto
    Black
    Brown Buc Brown
  • Authentic Original™ Veg Re-Tan Leather Boat Shoe, Tan, dynamic

    Men's Authentic Original™ Veg Re-Tan Leather Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Java
    Navy
    Tan
  • Authentic Original™ Veg Re-Tan Leather Boat Shoe, Navy, dynamic

    Men's Authentic Original™ Veg Re-Tan Leather Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Java
    Navy
    Tan
  • Authentic Original™ Veg Re-Tan Leather Boat Shoe, Java, dynamic

    Men's Authentic Original™ Veg Re-Tan Leather Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Java
    Navy
    Tan
  • Sperry x Brooks Brothers Authentic Original™ Kiltie Boat Shoe, Classic Brown, dynamic

    Men's Sperry x Brooks Brothers Authentic Original™ Kiltie Boat Shoe

    price C$ 250.00
    Wishlist Added to Wishlist
    Quick Add
  • Sperry x Brooks Brothers Authentic Original™ Boat Shoe, Pink Multi, dynamic

    Women's Sperry x Brooks Brothers Authentic Original™ Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
  • Authentic Original™ Cross Lace Boat Shoe, Tan, dynamic

    Men's Authentic Original™ Cross Lace Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Tan
    Black
    Brown
    Navy
  • Authentic Original™ Cross Lace Boat Shoe, Brown, dynamic

    Men's Authentic Original™ Cross Lace Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Tan
    Black
    Brown
    Navy
  • Authentic Original™ Cross Lace Boat Shoe, Navy, dynamic

    Men's Authentic Original™ Cross Lace Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Tan
    Black
    Brown
    Navy
  • Authentic Original™ Cross Lace Boat Shoe, Black, dynamic

    Men's Authentic Original™ Cross Lace Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Tan
    Black
    Brown
    Navy
  • Authentic Original™ Whitewashed Boat Shoe, Light Blue, dynamic

    Men's Authentic Original™ Whitewashed Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Black
    Light Blue
    Taupe
  • Authentic Original™ Whitewashed Boat Shoe, Taupe, dynamic

    Men's Authentic Original™ Whitewashed Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Black
    Light Blue
    Taupe
  • Authentic Original™ Whitewashed Boat Shoe, Black, dynamic

    Men's Authentic Original™ Whitewashed Boat Shoe

    price C$ 145.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Black
    Light Blue
    Taupe
  • Starfish 1-Eye Palm Embossed Boat Shoe, Rose, dynamic

    Women's Starfish 1-Eye Palm Embossed Boat Shoe

    price C$ 140.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Grey
    Rose
    Tan
  • Starfish 1-Eye Palm Embossed Boat Shoe, Grey, dynamic

    Women's Starfish 1-Eye Palm Embossed Boat Shoe

    price C$ 140.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Grey
    Rose
    Tan
  • Starfish 1-Eye Palm Embossed Boat Shoe, Tan, dynamic

    Women's Starfish 1-Eye Palm Embossed Boat Shoe

    price C$ 140.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Grey
    Rose
    Tan
  • Billfish™ 3-Eye Leather Boat Shoe, Black, dynamic

    Men's Billfish™ 3-Eye Leather Boat Shoe

    price C$ 160.00
    Wishlist Added to Wishlist
    Quick Add
  • Gold Cup™ Billfish™ PLUSHWAVE™ Boat Shoe, Tan, dynamic

    Men's Gold Cup™ Billfish™ PLUSHWAVE™ Boat Shoe

    price C$ 250.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Tan
    Amaretto
  • Gold Cup™ Billfish™ PLUSHWAVE™ Boat Shoe, Amaretto, dynamic

    Men's Gold Cup™ Billfish™ PLUSHWAVE™ Boat Shoe

    price C$ 250.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Tan
    Amaretto
  • Freshfish Boat Shoe, Navy, dynamic

    Women's Freshfish Boat Shoe

    price C$ 140.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Grey
    Light Tan
    Navy
  • Freshfish Boat Shoe, Light Tan, dynamic

    Women's Freshfish Boat Shoe

    price C$ 140.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Grey
    Light Tan
    Navy
  • Freshfish Boat Shoe, Grey, dynamic

    Women's Freshfish Boat Shoe

    price C$ 140.00
    Wishlist Added to Wishlist
    Quick Add
    3 Colors
    Grey
    Light Tan
    Navy
  • Unisex Sperry x Pleasures Authentic Original™ 3-Eye Vibram Boat Shoe, Black, dynamic

    Unisex Sperry x Pleasures Authentic Original™ 3-Eye Vibram Boat Shoe

    price C$ 230.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Blue
  • Unisex Sperry x Pleasures Authentic Original™ 3-Eye Vibram Boat Shoe, Blue, dynamic

    Unisex Sperry x Pleasures Authentic Original™ 3-Eye Vibram Boat Shoe

    price C$ 230.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Blue
  • Authentic Original™ Lug 3-Eye Boat Shoe, Brown, dynamic

    Men's Authentic Original™ Lug 3-Eye Boat Shoe

    price C$ 210.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Brown
    Tan
  • Authentic Original™ Lug 3-Eye Boat Shoe, Tan, dynamic

    Men's Authentic Original™ Lug 3-Eye Boat Shoe

    price C$ 210.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Brown
    Tan
  • Sperry x Herschel Authentic Original™ Lug 3-Eye, Black, dynamic

    Men's Sperry x Herschel Authentic Original™ Lug 3-Eye

    price C$ 175.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Sperry x Herschel Authentic Original™ Lug 3-Eye, Tan, dynamic

    Men's Sperry x Herschel Authentic Original™ Lug 3-Eye

    price C$ 175.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Black
    Tan
  • Highland Platform Boat Shoe, Baby Blue, dynamic

    Women's Highland Platform Boat Shoe

    price C$ 170.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Tan
    Baby Blue
  • Highland Platform Boat Shoe, Tan, dynamic

    Women's Highland Platform Boat Shoe

    price C$ 170.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Tan
    Baby Blue
  • Unisex Captain's Tassel Loafer, Ivory, dynamic

    Unisex Captain's Tassel Loafer

    price C$ 180.00
    Wishlist Added to Wishlist
    Quick Add
  • Seaport Tri-Tone Penny Loafer, Pink, dynamic

    Women's Seaport Tri-Tone Penny Loafer

    price C$ 140.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Green
    Pink
  • Seaport Tri-Tone Penny Loafer, Green, dynamic

    Women's Seaport Tri-Tone Penny Loafer

    price C$ 140.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Green
    Pink
  • Captain's Crepe Bow Oxford, Ivory, dynamic

    Women's Captain's Crepe Bow Oxford

    price C$ 220.00
    Wishlist Added to Wishlist
    Quick Add
  • Kennedy Wedge, Navy, dynamic

    Women's Kennedy Wedge

    price C$ 130.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Navy
    Tan
  • Kennedy Wedge, Tan, dynamic

    Women's Kennedy Wedge

    price C$ 130.00
    Wishlist Added to Wishlist
    Quick Add
    2 Colors
    Navy
    Tan
  • SeaCycled™ Captain's Moc Boat Baja, Navy, dynamic

    Men's SeaCycled™ Captain's Moc Boat Baja

    price C$ 100.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Black
    Blue
    Navy
    Taupe
  • SeaCycled™ Captain's Moc Boat Baja, Black, dynamic

    Men's SeaCycled™ Captain's Moc Boat Baja

    price C$ 100.00
    Wishlist Added to Wishlist
    Quick Add
    4 Colors
    Black
    Blue
    Navy
    Taupe
  • SeaCycled™ Captain's Moc Boat Baja, Taupe, dynamic

    Men's SeaCycled™ Captain's Moc Boat Baja

    price C$ 100.00
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    4 Colors
    Black
    Blue
    Navy
    Taupe

Date Night

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