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Women's Cute Casual Boots & Best Monogrammed Slippers

Comfortable High Heels, Women's Loafers & Casual Shoes

When making our casual shoes for women, our designers take the timeless styles you love, and update them with features to make them comfortable enough for everyday wear. Our cute, casual boots are made with luxurious materials like rich suede and buttery leather, and boast features like side zips and removable padded footbeds for comfort. Our comfortable high heels, with their stacked block heels and approachable height, make transitioning from day to night effortless. Pair them with your favorite jeans and a jacket, and you’re ready for anything! Our comfortable women’s loafers are a classic style staple which is always ready to slip on and go. They’re also comfortable with all-year wear with breathable leather footbeds, wide size options, and shock-absorbing rubber outsoles.

Our casual shoes and boots for women are easy, stylish day-to-night options with a focus on comfort. Our casual boots or booties look just as cute during back-to-back meetings as they will at the airport on your way to your next tropical vacation. Our comfortable high heels are a perfect way to add a little extra height at the office, and they’re cute enough to give you an excuse to join your coworkers for drinks after work. On weekends, slip our comfortable women’s loafers on, and you’ll be ready for anything, whether you’re taking the kids to the movies or checking out a quirky flea market on your next road trip.

Our comfortable, casual shoes for women are as versatile as you are. With styles like cute, casual boots, stylish yet comfortable high heels, and effortless, timeless loafers, you’ll never be uncomfortable wearing the styles you love.

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Products 25 - 36 of 157
  • Women's Wide Comfort Driving Shoes
    Women's Wide Comfort Driving Shoes
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    Women's Wide Comfort Driving Shoes
    $44.97 $84.95

    Women's Wide Comfort Driving Shoes
    Item #498721-6U
    All the comfort and flexibility of a classic driving moccasin but with modern style updates. Rich suede, a delightful buckle detail and a rubber heel to prevent wear are all in keeping with the tradition of this style. A leather-covered, cushioned foam footbed makes it one of the most comfortable shoes you’ll own. They might make you a little nostalgic for long Sunday afternoon drives of yore.
    Item #498721-6U
    Color:
    $44.97 - $84.95
    Size: Please Select
    • 6H
      $44.97 $84.95
    • 7
      $44.97 $84.95
    • 7H
      $44.97 $84.95
    • 8H
      $44.97 $84.95
  • Women's D'Orsay Flats
    Women's D'Orsay Flats
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    Women's D'Orsay Flats
    $39.97 $65.00

    Women's D'Orsay Flats
    Item #483800-6U
    Another example of our subtle, simplistic flats made to wear your way. A flattering pointed toe elongates legs and is ideal for livening up your jeans, skirts or dresses. Mix and match these versatile flats with any outfit of your choosing, whether it be work or play you have in mind.
    Item #483800-6U
    Color:
    $39.97 - $65.00
    Size: Please Select
    • 6
      $39.97 $65.00
    • 7
      $39.97 $65.00
    • 8
      $39.97 $65.00
  • School Uniform Women's Sperry Koifish Boat Shoes
    School Uniform Women's Sperry Koifish Boat Shoes
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    School Uniform Women's Sperry Koifish Boat Shoes
    $90.00

    School Uniform Women's Sperry Koifish Boat Shoes
    Item #506425-5X
    Sperry Koifish Boat Shoes look and feel great in the classroom. The EVA foam midsole keeps feet comfortable and supported when walking down the halls and the adjustable 360° Lacing System™  ensures the most secure fit possible.
    Item #506425-5X
    Color:
    $90.00
    Size: Please Select
    • 5
      $90.00
    • 6
      $90.00
    • 6H
      $90.00
    • 7
      $90.00
    • 7H
      $90.00
    • 8
      $90.00
    • 8H
      $90.00
    • 9
      $90.00
    • 9H
      $90.00
    • 10
      $90.00
    • 11
      $90.00
  • Women's Sperry Koifish Boat Shoes
    Women's Sperry Koifish Boat Shoes
    uick View
    Women's Sperry Koifish Boat Shoes
    $90.00

    Women's Sperry Koifish Boat Shoes
    Item #506425-AJ
    Sperry Koifish Boat Shoes look and feel great. The EVA foam midsole keeps feet comfortable and supported when walking and the adjustable 360° Lacing System™  ensures the most secure fit possible.
    Item #506425-AJ
    Color:
    $90.00
    Size: Please Select
    • 5
      $90.00
    • 6
      $90.00
    • 6H
      $90.00
    • 7
      $90.00
    • 7H
      $90.00
    • 8
      $90.00
    • 8H
      $90.00
    • 9
      $90.00
    • 9H
      $90.00
    • 10
      $90.00
    • 11
      $90.00
  • Women's Elastic Espadrille Shoes
    Women's Elastic Espadrille Shoes
    Women's Elastic Espadrille Shoes
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    Women's Elastic Espadrille Shoes
    $44.97 $74.95

    Women's Elastic Espadrille Shoes
    Item #495770-6U
    Comfortable, light, just what a sunny day shoe should be. The classic look of espadrilles, thanks to the jute-wrapped midsole, with an elastic band at the vamp for ease and comfort. Perfect to take you through the sunny season in style.
    Item #495770-6U
    Color:
    $44.97 - $74.95
    $44.97 - $74.95
    Size: Please Select
    • 6
      $44.97 $74.95
    • 6H
      $44.97 $74.95
    • 7
      $44.97 $74.95
    • 7H
      $44.97 $74.95
    • 8
      $44.97 $74.95
    • 8H
      $44.97 $74.95
    • 9
      $44.97 $74.95
    • 9H
      $44.97 $74.95
    • 10
      $44.97 $74.95
    • 11
      $44.97 $74.95
    Size: Please Select
    • 6
      $44.97 $74.95
    • 6H
      $44.97 $74.95
    • 7
      $44.97 $74.95
    • 8
      $44.97 $74.95
    • 8H
      $44.97 $74.95
    • 9
      $44.97 $74.95
    • 10
      $44.97 $74.95
  • Women's Wide Scallop Driving Shoes
    Women's Wide Scallop Driving Shoes
    Women's Wide Scallop Driving Shoes
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    Women's Wide Scallop Driving Shoes
    $44.97 $84.95

    Women's Wide Scallop Driving Shoes
    Item #487807-6U
    All the comfort and flexibility of a traditional driving moccasin but with modern style updates. It starts with tumbled leather or oiled suede and add a delightful scallop detail with metal tipped tie. The podded rubber sole with rubber heel detail is in keeping with a traditional driving shoe style, and a thick cushioned leather footbed makes it one of the most comfortable shoes you’ll own. They might convince you to bring back those long Sunday afternoon drives of yore.
    Item #487807-6U
    Color:
    $44.97 - $84.95
    $44.97 - $84.95
    Size: Please Select
    • 6
      $44.97 $84.95
    • 6H
      $44.97 $84.95
    • 7
      $44.97 $84.95
    • 7H
      $44.97 $84.95
    Size: Please Select
    • 6
      $44.97 $84.95
    • 7
      $44.97 $84.95
    • 7H
      $44.97 $84.95
  • Women's Lightweight Gatas Shoes
    Women's Lightweight Gatas Shoes
    Women's Lightweight Gatas Shoes
    Women's Lightweight Gatas Shoes
    Women's Lightweight Gatas Shoes
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    Women's Lightweight Gatas Shoes
    $24.97 $49.95

    Women's Lightweight Gatas Shoes
    Item #495762-6U
    Cute, laid-back design and did we mention ... Comfortable! You’ll feel like you’re walking on a cloud. Textile upper with elastic trim on vamp and grosgrain collar. With a flexible and lightweight outsole for all-day comfort and cushion.
    Item #495762-6U
    Color:
    $24.97 - $49.95
    $24.97 - $49.95
    $24.97 - $49.95
    $24.97 - $49.95
    Size: Please Select
    • 6
      $24.97 $49.95
    • 6H
      $24.97 $49.95
    • 7
      $24.97 $49.95
    • 7H
      $24.97 $49.95
    • 8
      $24.97 $49.95
    • 8H
      $24.97 $49.95
    • 9
      $24.97 $49.95
    • 9H
      $24.97 $49.95
    • 10
      $24.97 $49.95
    • 11
      $24.97 $49.95
    Size: Please Select
    • 6
      $24.97 $49.95
    • 6H
      $24.97 $49.95
    • 7
      $24.97 $49.95
    • 7H
      $24.97 $49.95
    • 8
      $24.97 $49.95
    • 8H
      $24.97 $49.95
    • 9
      $24.97 $49.95
    • 9H
      $24.97 $49.95
    • 10
      $24.97 $49.95
    • 11
      $24.97 $49.95
    Size: Please Select
    • 6H
      $24.97 $49.95
    • 7
      $24.97 $49.95
    • 7H
      $24.97 $49.95
    • 8
      $24.97 $49.95
    • 8H
      $24.97 $49.95
    • 9
      $24.97 $49.95
    • 9H
      $24.97 $49.95
    • 11
      $24.97 $49.95
    Size: Please Select
    • 7H
      $24.97 $49.95
    • 8
      $24.97 $49.95
    • 8H
      $24.97 $49.95
    • 9
      $24.97 $49.95
    • 9H
      $24.97 $49.95
    • 10
      $24.97 $49.95
    • 11
      $24.97 $49.95
  • Women's Wide Scallop Ballet Flats
    Women's Wide Scallop Ballet Flats
    Women's Wide Scallop Ballet Flats
    Women's Wide Scallop Ballet Flats
    Women's Wide Scallop Ballet Flats
    Women's Wide Scallop Ballet Flats
    Women's Wide Scallop Ballet Flats
    Women's Wide Scallop Ballet Flats
    Women's Wide Scallop Ballet Flats
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    Women's Wide Scallop Ballet Flats
    $29.97 $64.95

    Women's Wide Scallop Ballet Flats
    Item #483797-6U
    Feminine, traditional, and versatile, with a touch of scalloped detailing to set them apart from your typical ballets. Foam footbeds cushion you every step of the way, making them perfect for running errands in style, dressing up your jeans and tees, or walking around your office.
    Item #483797-6U
    Color:
    $29.97 - $64.95
    $29.97 - $64.95
    $29.97 - $64.95
    $29.97 - $64.95
    $29.97 - $64.95
    $29.97 - $64.95
    $29.97 - $64.95
    $29.97 - $64.95
    Size: Please Select
    • 6
      $29.97 $64.95
    • 6H
      $29.97 $64.95
    • 7
      $29.97 $64.95
    • 7H
      $29.97 $64.95
    • 8
      $29.97 $64.95
    • 8H
      $29.97 $64.95
    • 9
      $29.97 $64.95
    • 9H
      $29.97 $64.95
    • 10
      $29.97 $64.95
    Size: Please Select
    • 6
      $29.97 $64.95
    • 6H
      $29.97 $64.95
    • 7
      $29.97 $64.95
    • 7H
      $29.97 $64.95
    • 8
      $29.97 $64.95
    • 8H
      $29.97 $64.95
    • 9
      $29.97 $64.95
    • 9H
      $29.97 $64.95
    • 10
      $29.97 $64.95
    • 11
      $29.97 $64.95
    Size: Please Select
    • 6
      $29.97 $64.95
    • 6H
      $29.97 $64.95
    • 7
      $29.97 $64.95
    • 7H
      $29.97 $64.95
    • 8
      $29.97 $64.95
    • 8H
      $29.97 $64.95
    Size: Please Select
    • 6
      $29.97 $64.95
    • 7
      $29.97 $64.95
    • 7H
      $29.97 $64.95
    • 8H
      $29.97 $64.95
    Size: Please Select
    • 6
      $29.97 $64.95
    • 6H
      $29.97 $64.95
    • 7
      $29.97 $64.95
    • 7H
      $29.97 $64.95
    • 8
      $29.97 $64.95
    • 8H
      $29.97 $64.95
    • 9
      $29.97 $64.95
    • 9H
      $29.97 $64.95
    • 10
      $29.97 $64.95
    • 11
      $29.97 $64.95
    Size: Please Select
    • 6
      $29.97 $64.95
    • 6H
      $29.97 $64.95
    • 7
      $29.97 $64.95
    • 8H
      $29.97 $64.95
    • 9
      $29.97 $64.95
    • 10
      $29.97 $64.95
    Size: Please Select
    • 6
      $29.97 $64.95
    • 6H
      $29.97 $64.95
    • 7
      $29.97 $64.95
    • 7H
      $29.97 $64.95
    • 8H
      $29.97 $64.95
    • 9
      $29.97 $64.95
    • 9H
      $29.97 $64.95
    Size: Please Select
    • 6
      $29.97 $64.95
    • 6H
      $29.97 $64.95
    • 7
      $29.97 $64.95
    • 7H
      $29.97 $64.95
    • 8
      $29.97 $64.95
    • 8H
      $29.97 $64.95
    • 10
      $29.97 $64.95
  • Women's Cross Strap Espadrille Flats
    Women's Cross Strap Espadrille Flats
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    Women's Cross Strap Espadrille Flats
    $39.97 $74.95

    Women's Cross Strap Espadrille Flats
    Item #491399-6U
    So lovely you’ll want to wear them all day, and comfortable enough to get away with it. The wrapped jute midsole dials down the dressiness and keeps them just casual enough for shorts, capris and jeans while the straps and zigzag trim are perfect for skirts and dresses.
    Item #491399-6U
    Color:
    $39.97 - $74.95
    Size: Please Select
    • 6
      $39.97 $74.95
    • 6H
      $39.97 $74.95
    • 7
      $39.97 $74.95
    • 7H
      $39.97 $74.95
    • 8
      $39.97 $74.95
    • 8H
      $39.97 $74.95
    • 9
      $39.97 $74.95
    • 9H
      $39.97 $74.95
    • 11
      $39.97 $74.95
  • Women's Elastic Embroidered Espadrille Shoes
    Women's Elastic Embroidered Espadrille Shoes
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    Women's Elastic Embroidered Espadrille Shoes
    $39.97 $79.95

    Women's Elastic Embroidered Espadrille Shoes
    Item #499316-6U
    The classic look of espadrilles, thanks to the jute-wrapped midsole, with an embroidered wheel at the helm. (Just a little tip of the cap to our nautical heritage.) An elastic band at the instep provides ease and comfort.
    Item #499316-6U
    Color:
    $39.97 - $79.95
    Size: Please Select
    • 6H
      $39.97 $79.95
    • 7
      $39.97 $79.95
    • 7H
      $39.97 $79.95
    • 8
      $39.97 $79.95
    • 8H
      $39.97 $79.95
    • 9
      $39.97 $79.95
    • 9H
      $39.97 $79.95
    • 10
      $39.97 $79.95
    • 11
      $39.97 $79.95
  • Women's Gatas Slip-ons
    Women's Gatas Slip-ons
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    Women's Gatas Slip-ons
    $24.97 $49.95

    Women's Gatas Slip-ons
    Item #481519-6U
    Our queens of comfort.  A footbed that offers cushion and stability, a rich cotton upper and a flexible, durable outsole made of shock-absorbing Rubberlon® are just a few things to love about these shoes. Their cute, laid-back design and easy slip-on style seals the deal when it comes to being in complete, casual comfort. Perfect for the poolside, running errands and almost anything in between.
    Item #481519-6U
    Color:
    $24.97 - $49.95
    Size: Please Select
    • 6
      $24.97 $49.95
    • 7H
      $24.97 $49.95
    • 8
      $24.97 $49.95
    • 9
      $24.97 $49.95
    • 9H
      $24.97 $49.95
  • Women's Comfort Mary Jane Shoes
    Women's Comfort Mary Jane Shoes
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    Women's Comfort Mary Jane Shoes
    $34.97 $59.95

    Women's Comfort Mary Jane Shoes
    Item #487563-6U
    A durable rubber bottom with sturdy traction makes every step in this Mary Jane a sure one. Elasticated straps, super soft footbed (it’s removable for quick cleaning) and a pretty suede toe cap make easy even easier.
    Item #487563-6U
    Color:
    $34.97 - $59.95
    Size: Please Select
    • 6
      $34.97 $59.95
    • 6H
      $34.97 $59.95

Our cute, casual shoes for women are easy to slip on and don’t hurt your feet even if you wear them for hours.

Our comfortable, casual shoes for women are designed to take in style, whether you’re headed to work, running errands, or meeting friends for dinner and drinks. Pair our cute casual boots with a dress for work, or wear them with jeans and a statement necklace for a night out with friends. Try a pair of comfortable high heels with a sturdy block heel that gives you the lift your legs want, but still makes sure you’re well supported. The understated versatility of our comfortable women’s loafers will never go out of style – get yours in rich, buttery suede or luxurious calf hair for a year-round classic you’ll want to wear every day.

Our casual shoes for women are designed in timeless, classic styles. Try our cute, casual boots or booties in rich, color-soaked suede with a stunning saturated finish that will complement your favorite jeans, day or night. Our comfortable high heels are perfect for the big meeting at work, without giving you blisters or pinched toes. On busy weekends, our comfortable loafers are your go-to footwear for style in every step.

Our casual shoes for women never skimp on comfort to bring you the styles you love. Our comfortable and cute casual boots are available in wide sizes, so your feet will never feel pinched or cramped. Pair our comfortable high heels with a pretty dress for your next wedding or party, and you can dance all night long thanks to styles with supportive block heels, removable cushioned footbeds, and a wide range of heel heights. Our comfortable loafers are as practical as they’re versatile – wear them shopping or sightseeing on your next vacation, and the removable cushioned footbed will keep your feet supported and comfortable all day long.

Our team proudly designs casual shoes for women who need comfort, but can’t sacrifice style. Our cute, comfortable boots and booties are made with gorgeous materials like leather and suede, and boast features like cushioned footbeds and wide sizes so they’re comfortable enough for everyday wear. Our high heels add comfortable functionality like block heels and reasonable heel heights to the classic styles you love. Whether you choose comfortable women’s loafers, feminine ballet flats, or high-heeled riding boots, our casual women’s shoes are sure to keep you comfortable and stylish from 9 to 5 and beyond, Guaranteed. Period.® If you’re not satisfied with any item, simply return it to us at any time for an exchange or refund of its purchase price.  
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