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Kids Boots & Boy's Casual Dress Shoes

Boys’ Winter Boots, Snow Boots & House Slippers

With our boys’ casual shoes ranging in sizes from toddler to big kid. We make kids’ boots for tackling the trails and sandals for days on the beach, so you can find shoes for every season. Our casual dress shoes are a nice choice for school days or special occasions requiring a shoe a step up from a sneaker. Our winter boots resist water to keep feet warm and dry on long winter day adventures.

Our boys’ casual shoes are carefully made to our legendary standards, so your child will probably outgrow his sneakers or snow boots before they outwear them. We make kids’ boots with rip and grip adjustable straps for a customized fit and the reflective tape for increased visibility during evening outdoor play. You’ll want our casual dress shoes and boots on hand so your kids are ready for any adventure that comes their way. Our winter boots are great for snow days and muddy spring days when fresh outdoor air is calling.

Our boys’ casual shoes will keep your kids’ feet comfortable all year round. We have kids’ boots for cold winter days and casual dress shoes for everyday wear.

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Products 1 - 12 of 55
  • Boys Chukka Boots

    Boys Chukka Boots

    Classic chukka boots with innovative construction allowing him to simply slip on and go, or wear as traditional lace-ups. Perfect for school and anything beyond!
    Item #489204-A7
    Color:
    $49.95
    $49.95
    $49.95
    Size: Please Select
    • 9
      $49.95
    • 10
      $49.95
    • 13
      $49.95
    • 1
      $49.95
    • 2
      $49.95
    • 3
      $49.95
    • 4
      $49.95
    • 5
      $49.95
    • 6
      $49.95
    • 7
      $49.95
    Size: Please Select
    • 9
      $49.95
    • 10
      $49.95
    • 11
      $49.95
    • 12
      $49.95
    • 13
      $49.95
    • 1
      $49.95
    • 2
      $49.95
    • 3
      $49.95
    • 4
      $49.95
    • 5
      $49.95
    • 6
      $49.95
    • 7
      $49.95
    Size: Please Select
    • 9
      $49.95
    • 10
      $49.95
    • 11
      $49.95
    • 12
      $49.95
    • 13
      $49.95
    • 1
      $49.95
    • 2
      $49.95
    • 3
      $49.95
    • 4
      $49.95
    • 5
      $49.95
    • 6
      $49.95
    • 7
      $49.95
  • Kids All Weather Moc Shoes

    Kids All Weather Moc Shoes

    All Weather Mocs™ feature a brand new sole with reinforced toes for rugged recess play. Classic looks and A+ comfort lend them to everyday wear. Whether worn with jeans and tees or khakis and button-downs, All-Weather Mocs fit the look. Complete with rubber soles for traction. Elastic gore provides a customized fit and makes them easy to slide on/off. Cushioned, antimicrobial footbed finish helps keep feet fresh and comfortable.
    Item #483155-A7
    Color:
    $19.99 - $39.00
    $19.99 - $39.00
    $19.99 - $39.00
    Size: Please Select
    • 9
      $19.99 $39.95
    • 10
      $19.99 $39.95
    • 11
      $19.99 $39.95
    • 12
      $19.99 $39.95
    • 13
      $19.99 $39.95
    • 1
      $19.99 $39.95
    • 2
      $19.99 $39.95
    • 3
      $19.99 $39.95
    • 4
      $19.99 $39.95
    • 5
      $19.99 $39.95
    • 6
      $19.99 $39.95
    • 7
      $19.99 $39.95
    Size: Please Select
    • 9
      $19.99 $39.95
    • 10
      $19.99 $39.95
    • 1
      $19.99 $39.95
    • 2
      $19.99 $39.95
    • 4
      $19.99 $39.95
    • 5
      $19.99 $39.95
    • 7
      $19.99 $39.95
    Size: Please Select
    • 9
      $19.99 $39.95
    • 2
      $19.99 $39.95
    • 4
      $19.99 $39.95
    • 5
      $19.99 $39.95
    • 6
      $19.99 $39.95
    • 7
      $19.99 $39.95
  • Kids Sperry Colton Loafers

    Kids Sperry Colton Loafers

    Grab the Sperry Colton loafer for days when he’s feeling a little fancy. With a brush-off leather finish just right for dress, the Colton loafer has plenty of built-in comfort features for growing boys. Save time in their morning routine with the slip-on design and flexible outsole for quick on and off.
    Item #506433-A7
    Color:
    $55.00
    $55.00
    Size: Please Select
    • 13
      $55.00
    • 1
      $55.00
    • 2
      $55.00
    • 3
      $55.00
    • 4
      $55.00
    • 5
      $55.00
    Size: Please Select
    • 13
      $55.00
    • 1
      $55.00
    • 2
      $55.00
    • 3
      $55.00
    • 4
      $55.00
    • 5
      $55.00
    • 6
      $55.00
    • 7
      $55.00
  • Kids Wide All Weather Moc Shoes

    Kids Wide All Weather Moc Shoes

    All Weather Mocs™ feature a brand new sole with reinforced toes for rugged recess play. Classic looks and A+ comfort lend them to everyday wear. Whether worn with jeans and tees or khakis and button-downs, All-Weather Mocs fit the look. Complete with rubber soles for traction. Elastic gore provides a customized fit and makes them easy to slide on/off. Cushioned, antimicrobial footbed finish helps keep feet fresh and comfortable.
    Item #483155-A7
    Color:
    $19.99 - $39.00
    $19.99 - $39.00
    $19.99 - $39.00
    Size: Please Select
    • 9
      $19.99 $39.00
    • 10
      $19.99 $39.00
    • 11
      $19.99 $39.00
    • 12
      $19.99 $39.00
    • 13
      $19.99 $39.00
    • 1
      $19.99 $39.00
    • 2
      $19.99 $39.00
    • 3
      $19.99 $39.00
    • 4
      $19.99 $39.00
    • 5
      $19.99 $39.00
    • 6
      $19.99 $39.00
    • 7
      $19.99 $39.00
    Size: Please Select
    • 9
      $19.99 $39.00
    • 10
      $19.99 $39.00
    • 11
      $19.99 $39.00
    • 12
      $19.99 $39.00
    • 13
      $19.99 $39.00
    • 1
      $19.99 $39.00
    • 2
      $19.99 $39.00
    • 3
      $19.99 $39.00
    • 4
      $19.99 $39.00
    • 5
      $19.99 $39.00
    Size: Please Select
    • 9
      $19.99 $39.00
    • 10
      $19.99 $39.00
    • 11
      $19.99 $39.00
    • 12
      $19.99 $39.00
    • 1
      $19.99 $39.00
    • 2
      $19.99 $39.00
    • 3
      $19.99 $39.00
    • 4
      $19.99 $39.00
    • 5
      $19.99 $39.00
    • 6
      $19.99 $39.00
  • Boys Slip-on Oxfords

    Boys Slip-on Oxfords

    Classic oxford styling with kid-tastic convenience, thanks to the interior elastic gores that let him wear this timeless shoe with or without laces!
    Item #489203-A7
    Color:
    $44.95
    $44.95
    $44.95
    Size: Please Select
    • 9
      $44.95
    • 10
      $44.95
    • 11
      $44.95
    • 12
      $44.95
    • 13
      $44.95
    • 1
      $44.95
    • 2
      $44.95
    • 3
      $44.95
    • 4
      $44.95
    • 5
      $44.95
    • 6
      $44.95
    • 7
      $44.95
    Size: Please Select
    • 9
      $44.95
    • 10
      $44.95
    • 11
      $44.95
    • 12
      $44.95
    • 13
      $44.95
    • 1
      $44.95
    • 2
      $44.95
    • 3
      $44.95
    • 4
      $44.95
    • 5
      $44.95
    Size: Please Select
    • 9
      $44.95
    • 10
      $44.95
    • 11
      $44.95
    • 12
      $44.95
    • 13
      $44.95
    • 1
      $44.95
    • 2
      $44.95
    • 3
      $44.95
    • 4
      $44.95
    • 5
      $44.95
    • 6
      $44.95
    • 7
      $44.95
  • Toddler All Weather Moccasins

    Toddler All Weather Moccasins

    All Weather Mocs™ feature reinforced toes for rugged recess play. Classic looks and A+ comfort lend them to everyday wear. Whether worn with jeans and tees or khakis and button-downs, All-Weather Mocs fit the look. Complete with deep-tread soles for traction. Elastic sides provide a giving fit and makes them easy to slide on/off. Cushioned, antimicrobial footbed finish reduces shoe odor.
    Item #393280-A7
    Color:
    $14.99 - $39.95
    $14.99 - $39.95
    $14.99 - $39.95
    $14.99 - $39.95
    Size: Please Select
    • 5
      $14.99 $39.95
    • 6
      $14.99 $39.95
    Size: Please Select
    • 5
      $14.99 $39.95
    Size: Please Select
    • 5
      $14.99 $39.95
    • 6
      $14.99 $39.95
    Size: Please Select
    • 5
      $14.99 $39.95
    • 6
      $14.99 $39.95
  • Kids Superga 2750 JVEL Classic Sneakers

    Kids Superga 2750 JVEL Classic Sneakers

    Superga® makes these kids’ sneakers great for everyday wear – from school to playground and back again. You can dress them up or down; their feet will always feel comfy and their steps secure.
    Item #492940-A7
    Color:
    $44.00
    $44.00
    Size: Please Select
    Size: Please Select
  • Boys Sperry Gamefish Boat Shoes

    Boys Sperry Gamefish Boat Shoes

    The Gamefish boat shoe was designed for a lighter, durable wear to carry them from class to class without making his feet hurt. Even better, these shoes were built to last, featuring a hand-sewn construction that will last through the entire year.
    Item #506430-A7
    Color:
    $60.00
    Size: Please Select
    • 13
      $60.00
    • 1
      $60.00
    • 2
      $60.00
    • 3
      $60.00
    • 4
      $60.00
    • 5
      $60.00
    • 6
      $60.00
    • 7
      $60.00
  • Toddler Superga 2750 JVEL Classic Sneakers

    Toddler Superga 2750 JVEL Classic Sneakers

    Superga® makes these kids’ sneakers great for everyday wear – from school to playground and back again. You can dress them up or down; their feet will always feel comfy and their steps secure.
    Item #492941-A7
    Color:
    $44.00
    $44.00
    $44.00
    $44.00
    Size: Please Select
    • 6H
      $44.00
    • 7
      $44.00
    • 8
      $44.00
    • 8H
      $44.00
    Size: Please Select
    • 6H
      $44.00
    Size: Please Select
    • 6H
      $44.00
    • 7
      $44.00
    Size: Please Select
    • 6H
      $44.00
    • 7
      $44.00
    • 8
      $44.00
    • 8H
      $44.00
  • Kids Expedition Insulated Winter Snow Boots

    Kids Expedition Insulated Winter Snow Boots

    We know kids need snow boots their feet can count on. So we built our new Expedition snow boots to brave the elements with a waterproof rubber shell and outsole. Plus, they match our warmest, waterproof Expedition parkas, too!

    To add even further adjustability and ease of entry, we recommend you loosen the bungee laces before trying them on. That way you can specialize for future wear without having to re-adjust every time.
    Item #501719-A7
    Color:
    $79.95
    $79.95
    $79.95
    Size: Please Select
    • 9
      $79.95
    • 10
      $79.95
    • 11
      $79.95
    • 13
      $79.95
    • 1
      $79.95
    • 2
      $79.95
    • 3
      $79.95
    • 4
      $79.95
    • 5
      $79.95
    • 6
      $79.95
    Size: Please Select
    • 9
      $79.95
    • 10
      $79.95
    • 1
      $79.95
    • 2
      $79.95
    • 3
      $79.95
    • 4
      $79.95
    • 5
      $79.95
    • 6
      $79.95
    • 7
      $79.95
    Size: Please Select
    • 9
      $79.95
    • 10
      $79.95
    • 3
      $79.95
    • 4
      $79.95
    • 5
      $79.95
    • 6
      $79.95
    • 7
      $79.95
  • Kids Snow Flurry Winter Boots

    Kids Snow Flurry Winter Boots

    Easy to get on and off, with 200 grams of insulation to keep them on their toes in the snow. Featuring our unique OpenWIDE™ construction designed to extend twice as wide so feet can easily slip inside. Plus, we’ve added more reflective tape for extra safety!
    Item #487522-A7
    Color:
    $59.95
    $59.95
    $59.95
    $59.95
    $59.95
    $59.95
    $59.95
    $59.95
    Size: Please Select
    • 9
      $59.95
    • 10
      $59.95
    • 11
      $59.95
    • 12
      $59.95
    • 13
      $59.95
    • 1
      $59.95
    • 2
      $59.95
    • 3
      $59.95
    • 4
      $59.95
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    Size: Please Select
    • 3
      $59.95
    • 4
      $59.95
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    Size: Please Select
    • 11
      $59.95
    • 12
      $59.95
    • 1
      $59.95
    • 2
      $59.95
    • 3
      $59.95
    • 4
      $59.95
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    Size: Please Select
    • 1
      $59.95
    • 2
      $59.95
    • 3
      $59.95
    • 4
      $59.95
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    Size: Please Select
    • 9
      $59.95
    • 10
      $59.95
    • 11
      $59.95
    • 12
      $59.95
    • 13
      $59.95
    • 1
      $59.95
    • 2
      $59.95
    • 3
      $59.95
    • 4
      $59.95
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    Size: Please Select
    • 9
      $59.95
    • 10
      $59.95
    • 11
      $59.95
    • 12
      $59.95
    • 13
      $59.95
    • 1
      $59.95
    • 2
      $59.95
    • 3
      $59.95
    • 4
      $59.95
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    Size: Please Select
    • 9
      $59.95
    • 10
      $59.95
    • 11
      $59.95
    • 12
      $59.95
    • 13
      $59.95
    • 1
      $59.95
    • 2
      $59.95
    • 3
      $59.95
    • 4
      $59.95
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    Size: Please Select
    • 9
      $59.95
    • 10
      $59.95
    • 11
      $59.95
    • 12
      $59.95
    • 13
      $59.95
    • 1
      $59.95
    • 2
      $59.95
    • 3
      $59.95
    • 4
      $59.95
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
  • Toddler Snow Flurry Winter Boots

    Toddler Snow Flurry Winter Boots

    Easy to get on and off, with 200 grams of insulation to keep them on their toes in the snow. Featuring our unique OpenWIDE™ construction designed to extend twice as wide so feet can easily slip inside. Plus, we’ve added more reflective tape for extra safety!
    Item #489340-A7
    Color:
    $59.95
    $59.95
    $59.95
    Size: Please Select
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    • 8
      $59.95
    Size: Please Select
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    • 8
      $59.95
    Size: Please Select
    • 5
      $59.95
    • 6
      $59.95
    • 7
      $59.95
    • 8
      $59.95

We make boys’ casual shoes and winter boots to keep kids’ feet comfortable and warm.

You can find quality boys’ casual shoes at Lands’ End for every season and occasion. Our kids’ boots are built to last longer. We have casual dress shoes designed for comfort when walking from class to class. Our winter boots are made with weatherproof materials to keep feet warm and dry on wet, cold days spent outside.

We have boys’ casual shoes for the warm months when outdoor play is non-stop. You can shift from kids’ boots to sandals and sneakers on days when the sun is shining and the kids are begging for a run to the playground. Our casual dress shoes with rubber outsoles provide great traction. Those winter boots come in handy during the warmer spring weather when mud abounds and your little one insists on hitting every puddle.

In the fall, our boys’ casual shoes will take your kids from the school halls to the backyard with ease. Our kids’ boots are just right for hiking trails as you enjoy the changing leaves and crisp autumn air. You can keep casual dress shoes clean and ready for school days when boots are used for weekend fun. Be sure to buy winter boots early in the season in case the first snowflakes start to fall sooner than expected.

Our boys’ casual shoes don’t take a back seat in the cold winter months. Wearing kids’ boots on the trek to school will keep feet warm and dry for the school day. You can pack our casual dress shoes in kids’ backpacks to wear during the school day, while their snow boots are ready by the door for recess and the walk home. Our winter boots are waterproof and insulated so sledding and snow forts are the only thing on your kid’s mind while playing in the snow.
Products 1 - 12 of 55