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Home Women Loafers & Oxfords
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    Drizzle Mid Calf Rain Boot NavyDrizzle Mid Calf Rain Boot Navy

    Drizzle Mid Calf Rain Boot Navy

    Stay dry and stylish with the ladies' Drizzle Mid Calf Rain Boot. These lightweight rain boots are crafted from rubber, for a fully-waterproof upper and feature molded Wave-Siping™ technology on the outsole, for grip in wet and dry conditions. These boots have a timeless...
    $15.00
    $59.99
    $15.00
    Unit price
    / per 
    • Navy
    Sale
    Drizzle Knee High Rain BootDrizzle Knee High Rain Boot

    Drizzle Knee High Rain Boot

    Stay dry and stylish with the ladies' Drizzle Knee High Rain Boot. These lightweight rain boots are crafted from rubber, for a fully-waterproof upper and feature molded Wave-Siping™ technology on the outsole, for grip in wet and dry conditions. These boots have a timeless...
    $17.50
    $69.99
    $17.50
    Unit price
    / per 
    • Black
    Sale
    Drizzle Chelsea Rain Boot Pine GreenDrizzle Chelsea Rain Boot Pine Green

    Drizzle Chelsea Rain Boot Pine Green

    Stay dry and stylish with the ladies' Drizzle Chelsea Rain Boot. These lightweight rain boots are crafted from rubber, for a fully-waterproof upper and feature molded Wave-Siping™ technology on the outsole, for grip in wet and dry conditions. These boots have a sleek, timeless...
    $12.50
    $49.99
    $12.50
    Unit price
    / per 
    • Pine green
    Sale
    Dakota Mid Winter BootsDakota Mid Winter Boots

    Dakota Mid Winter Boots

    From après-ski to jaunts around town, bear the elements in style all winter long with the ladies’ Dakota snow boot. Constructed with a waterproof leather upper, cold-rating to -20°C, and Sperry’s signature Wave-Siping™ for secure footing, this mid-shaft performance boot will keep you warm...
    $20.00
    $79.99
    $20.00
    Unit price
    / per 
    • Light brown

    Women Loafers & Oxfords

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    • Sale
      Seaport Penny Leather Loafer Black - 2Seaport Penny Leather Loafer Black - 2

      Seaport Penny Leather Loafer Black - 2

      This smart take on our classic Seaport Penny loafer is sure to stand out this fall. The premium leather upper has been meticulously crafted using traditional moccasin construction and has been done up with a striking exotic reptile finish that adds a touch of...
      $8.59
      $34.99
      $8.59
      Unit price
      / per 
      • Black
    • Sale
      Seaport Penny Leather Loafer BlackSeaport Penny Leather Loafer Black

      Seaport Penny Leather Loafer Black

      The Seaport Penny is our seafaring take on the classic penny loafer. This shoe pulls in the moccasin construction with a traditional penny loafer feel. Keep it preppy with white jeans and a blazer or wear it under pleated skirts and chino shorts. Moccasin...
      $10.00
      $39.99
      $10.00
      Unit price
      / per 
      • Black
    • Sale
      Port Driver Loafer BlackPort Driver Loafer Black

      Port Driver Loafer Black

      As sleek as ever, the Port Driver Loafer creates an effortless look by utilizing premium materials and hand-sewn construction. Keep it classic. Material: Leather Sole: Non-marking rubber outsole with signature Wave-Siping™ technology for enhanced traction Driver Loafer Casual Shoes Round Toe Flat Heel Slip-on
      $7.50
      $29.99
      $7.50
      Unit price
      / per 
      • Black
    • Sale
      Seaport Penny Leather Loafer Medium BeigeSeaport Penny Leather Loafer Medium Beige

      Seaport Penny Leather Loafer Medium Beige

      The Seaport Penny is our seafaring take on the classic penny loafer. This shoe pulls in the moccasin construction with a traditional penny loafer feel. Keep it preppy with white jeans and a blazer or wear it under pleated skirts and chino shorts. Moccasin...
      $7.50
      $29.99
      $7.50
      Unit price
      / per 
      • Medium beige
    • Sale
      Captain's Oxford Mary JaneCaptain's Oxford Mary Jane

      Captain's Oxford Mary Jane

      The ladies' Captain's Oxford Crepe Mary Jane sees a preppy icon get a fashionable makeover. Our iconic Captain's Oxford has been reimagined as a Mary Jane, with a chic nubuck leather upper, a metal buckle on the strap opening and a comfortable crepe sole...
      $22.50
      $89.99
      $22.50
      Unit price
      / per 
      • Linen Multi
    • Sale
      Wedge Cupsole Penny Ladies NavyWedge Cupsole Penny Ladies Navy

      Wedge Cupsole Penny Ladies Navy

      Take your preppy footwear up a notch with this ladies' Wedge Cupsole Penny Loafer. The upper is crafted from pure premium suede, rendered in smart shades that are sure to stand out. The wedged sole gives these an elevated look that'll have you standing...
      $7.50
      $29.99
      $7.50
      Unit price
      / per 
      • Navy
    • Sale
      Slim Loafer Blue MultiSlim Loafer Blue Multi

      Slim Loafer Blue Multi

      Slim, streamlined and stylish. The ladies' Slim Loafer is a modern take on a timeless classic. These loafers feature a knit upper, which has been streamlined and slimmed down to create a more elongated silhouette. A thin sole complements the overall look and is...
      $10.00
      $39.99
      $10.00
      Unit price
      / per 
      • Blue Multi
    • Sale
      Seaportwoven Tan Women's Oxfords & LoafersSeaportwoven Tan Women's Oxfords & Loafers

      Seaportwoven Tan Women's Oxfords & Loafers

      Our popular ladies' Seaport Loafer has been reimagined with a woven leather upper that brings a touch of style to any look. Crafted from soft premium leather, these classic loafers sit atop a molded Wave-Siping™ outsole that provides grip on wet and dry surfaces....
      $15.00
      $59.99
      $15.00
      Unit price
      / per 
      • Tan
    • Sale
      Seaport Penny Loafer Brown Primary MultiSeaport Penny Loafer Brown Primary Multi

      Seaport Penny Loafer Brown Primary Multi

      A classic that can be worn day after day, season after season. Our timeless Seaport Penny Loafer is crafted from pure leather, with traditional penny loafer detailing and moccasin stitching on the upper. A memory foam insole and flexible rubber sole offer superior comfort...
      $20.00
      $79.99
      $20.00
      Unit price
      / per 
      • Brown primary - multi
    • Sale
      Seaport Woven LoaferSeaport Woven Loafer

      Seaport Woven Loafer

      Our popular ladies' Seaport Loafer has been reimagined with a woven leather upper that brings a touch of style to any look. Crafted from soft premium leather, these classic loafers sit atop a molded Wave-Siping™ outsole that provides grip on wet and dry surfaces....
      $15.00
      $59.99
      $15.00
      Unit price
      / per 
      • White
    • Sale
      Gold Cup™ Driver Loafer - NavyGold Cup™ Driver Loafer - Navy

      Gold Cup™ Driver Loafer - Navy

      Part boat shoe, part driving shoe, the ladies' Gold Cup Driver unites two legendary styles using the utmost of attention. Crafted to the highest standard, it features a sumptuously soft leather upper, thin metal-tipped rope laces, 360° Lacing™, and Wave-Siping™ technology for sure footing....
      $17.50
      $69.99
      $17.50
      Unit price
      / per 
      • Navy
    • Sale
      Port Driving Moccasin SilverPort Driving Moccasin Silver

      Port Driving Moccasin Silver

      Our signature Port Driving Moccasin is ready to hit the road after you dock in port. Crafted from premium leather, with traditional moccasin stitching, this womens' driving shoe sits atop a podded rubber outsole with Wave-Siping™ technology for unparalleled traction on wet and dry...
      $12.50
      $49.99
      $12.50
      Unit price
      / per 
      • Silver
    • Sale
      Captain’s Oxford Mule TanCaptain’s Oxford Mule Tan

      Captain’s Oxford Mule Tan

      Inspired by the first casual shoe designed for captains, the ladies' Captain's Oxford Crepe Mule gives a preppy icon a fashionable makeover with a chic suede upper, a metal buckle and a comfortable crepe sole for a touch of contrast. Easily slipped on or...
      $16.00
      $64.99
      $16.00
      Unit price
      / per 
      • Tan
    • Sale
      Lounge Away SneakerLounge Away Sneaker

      Lounge Away Sneaker

      A shoe you’ll want to wear all the time, the Lounge Away Slip-On stands out in any crowd. Its easy-to-slip-into design features our signature 360° Lacing™ for a secure fit, a memory foam insole for a cushy feel, and a molded outsole with Wave-Siping™...
      $15.00
      $60.00
      $15.00
      Unit price
      / per 
      • Navy
    • Sale
      Lounge Away SneakerLounge Away Sneaker

      Lounge Away Sneaker

      A shoe you’ll want to wear all the time, the Lounge Away Slip-On stands out in any crowd. Its easy-to-slip-into design features our signature 360° Lacing™ for a secure fit, a memory foam insole for a cushy feel, and a molded outsole with Wave-Siping™...
      $15.00
      $60.00
      $15.00
      Unit price
      / per 
      • Natural
    • Sale
      Candyltt Ecru Women's Oxfords & LoafersCandyltt Ecru Women's Oxfords & Loafers

      Candyltt Ecru Women's Oxfords & Loafers

      A fun, lightweight take on a silhouette that's anchored in tradition. The Candy LTT sees our classic deck sneaker streamlined and reimagined with a rubber cupsole and a lightweight mesh upper that lets the summer sea breeze blow through. These versatile womens' sneakers can...
      $10.00
      $39.99
      $10.00
      Unit price
      / per 
      • Ecru
    • Sale
      Mira loafer Cream Multi Women's Oxfords & LoafersMira loafer Cream Multi Women's Oxfords & Loafers

      Mira loafer Cream Multi Women's Oxfords & Loafers

      A laid-back loafer, infused with the effortless cool of espadrilles. The ladies' Mira Loafer sees a traditional loafer upper, crafted with moccasin stitching construction and finished with decorative laces on the tongue. A classic rope midsole draws inspiration from summery espadrilles. Rendered in smart...
      $10.00
      $39.99
      $10.00
      Unit price
      / per 
      • Cream Multi
    • Sale
      Gold Cup™ Driver Loafer - Light BrownGold Cup™ Driver Loafer - Light Brown

      Gold Cup™ Driver Loafer - Light Brown

      Part boat shoe, part driving shoe, the ladies' Gold Cup Driver unites two legendary styles using the utmost of attention. Crafted to the highest standard, it features a sumptuously soft leather upper, thin metal-tipped rope laces, 360° Lacing™, and Wave-Siping™ technology for sure footing....
      $43.50
      $173.50
      $43.50
      Unit price
      / per 
      • Light brown
    • Sale
      Captainsox Light Pink Women's LeatherCaptainsox Light Pink Women's Leather

      Captainsox Light Pink Women's Leather

      This version of the Captain's Oxford puts a fresh spin on a coastal classic. An icon of preppy style, the Captain's Oxford has been done up in sumptuous nubuck, for a slightly textured look that's certain to elevate your outfits. The outsole is finished...
      $11.00
      $44.99
      $11.00
      Unit price
      / per 
      • Light Pink
    • Sale
      Slim Loafer BeigeSlim Loafer Beige

      Slim Loafer Beige

      Slim, streamlined and stylish. The ladies' Slim Loafer is a modern take on a timeless classic. These loafers feature a knit upper, which has been streamlined and slimmed down to create a more elongated silhouette. A thin sole complements the overall look and is...
      $10.00
      $39.99
      $10.00
      Unit price
      / per 
      • Beige
    Showing 1 -20 of 41 total
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