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Men's Casual Comfort Chukka Boots

When we introduced our comfort casual loafer last season, it was an instant hit. This season, we’re bringing that same comfort philosophy to the chukka boot. Built from the ground-up for comfort, style and versatility, it features a soft yet durable suede upper, comfortable mesh lining and shock-absorbing EVA footbed for all-day comfort. Wear it with cuffed jeans or with chinos and a blazer for a smart casual look.
Item #501740-A7
Color:
$99.95
$99.95
Size: Please Select
  • 8
    $99.95
  • 8H
    $99.95
  • 9
    $99.95
  • 9H
    $99.95
  • 10
    $99.95
  • 10H
    $99.95
  • 11
    $99.95
  • 11H
    $99.95
  • 12
    $99.95
  • 13
    $99.95
Size: Please Select
  • 8
    $99.95
  • 8H
    $99.95
  • 9
    $99.95
  • 9H
    $99.95
  • 10
    $99.95
  • 10H
    $99.95
  • 11
    $99.95
  • 11H
    $99.95
  • 12
    $99.95
  • 13
    $99.95

Features

  • Suede upper
  • Leather trim
  • Polyester mesh lining and twill vamp lining
  • EVA outsole
  • EVA footbed with polyester mesh cover
  • Lace-up closure
  • Imported

Shipping

Free shipping on orders $50 or more (US & Canada only)*

*Excludes monogramming, embroidery, gift boxing, gift cards, taxes and duties.

Upgrade to Expedited Shipping or UPS Express available for an additional fee (US Only).

Orders ship from our warehouse the next business day after your order is placed*

*If an order contains items with monogramming, embroidery, a logo or hemming, please allow additional business days for the entire order to ship. Backordered and preordered items ship separately.

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Complete Shipping Details

Returns

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.

Easy Returns

Return orders for free at any full line Sears® store (US only) or by mail using our Easy Return label found on your packing slip for a flat fee of $6.95 (US only, $9.95 for Canada). See our complete return policy for other international returns.

Free Shipping Offered on Exchanges (US and Canada Only)

Free shipping with re-order of the same item or items in a different color or size.

Complete Return Policy

Often bought together

  • Men's Wide Casual Comfort Chukka Boots

    Men's Wide Casual Comfort Chukka Boots

    When we introduced our comfort casual loafer last season, it was an instant hit. This season, we’re bringing that same comfort philosophy to the chukka boot. Built from the ground-up for comfort, style and versatility, it features a soft yet durable suede upper, comfortable mesh lining and shock-absorbing EVA footbed for all-day comfort. Wear it with cuffed jeans or with chinos and a blazer for a smart casual look.
    Item #501740-A7
    Color:
    $99.95
    $99.95
    Size: Please Select
    • 8
      $99.95
    • 8H
      $99.95
    • 9
      $99.95
    • 9H
      $99.95
    • 10
      $99.95
    • 10H
      $99.95
    • 11
      $99.95
    • 11H
      $99.95
    • 12
      $99.95
    • 13
      $99.95
    Size: Please Select
    • 8
      $99.95
    • 8H
      $99.95
    • 9
      $99.95
    • 9H
      $99.95
    • 10
      $99.95
    • 10H
      $99.95
    • 11
      $99.95
    • 11H
      $99.95
    • 12
      $99.95
    • 13
      $99.95
  • Men's Unlined Chelsea Duck Boots

    Men's Unlined Chelsea Duck Boots

    A classic boot for outdoor adventures in fall, spring or winter. Outside you’ll find an unlined leather upper, waterproof rubber shell and a grippy rubber outsole. Inside, a soft fabric lining for the rubber shell and a cushioned footbed lined with 400 grams of Thermolite insulation to fend off chills. Twin elastic gores make them easy to slip on and go. Pair with jeans and a buttondown for easy, casual style.
    Item #501734-A7
    Color:
    $99.95
    $99.95
    Size: Please Select
    • 8
      $99.95
    • 9
      $99.95
    • 10
      $99.95
    • 11
      $99.95
    • 12
      $99.95
    • 13
      $99.95
    Size: Please Select
    • 8
      $99.95
    • 9
      $99.95
    • 10
      $99.95
    • 11
      $99.95
    • 12
      $99.95
    • 13
      $99.95
  • Men's Unlined Duck Boots

    Men's Unlined Duck Boots

    Looking for the foundational piece of your fall uniform? Look no further. Duck boots are a classic for a reason. Just button up that flannel, slip into your favorite jeans, and pull on these boots for rugged, functional style that can serve as your go-to look all season long.
    Item #490642-A7
    Color:
    $99.95
    $99.95
    Size: Please Select
    • 8
      $99.95
    • 9
      $99.95
    • 10
      $99.95
    • 13
      $99.95
    Size: Please Select
    • 8
      $99.95
    • 9
      $99.95
    • 10
      $99.95
    • 11
      $99.95
    • 12
      $99.95
    • 13
      $99.95
  • Men's All Weather Lace-up Boots

    Men's All Weather Lace-up Boots

    You raved about the mocs, calling them “hard working” and “more comfortable than sneakers!” So now, we’re introducing the new best thing for the colder months: All Weather Lace-up Boots. With a comfort-first design and a rubber outsole that’s rugged enough for any terrain, these are sure to have you raving all over again. 
    Item #489099-A7
    Color:
    $59.99 - $99.95
    Size: Please Select
    • 8H
      $59.99 $99.95
    • 9
      $59.99 $99.95
    • 9H
      $59.99 $99.95
    • 10
      $59.99 $99.95
    • 10H
      $59.99 $99.95
    • 11
      $59.99 $99.95
    • 11H
      $59.99 $99.95
    • 12
      $59.99 $99.95
    • 13
      $59.99 $99.95
  • Men's Moc Chukka Boots

    Men's Moc Chukka Boots

    An amalgamation of moc-stitch styling and the chukka boot silhouette, our moc chukka boots are an easy-wearing, good-looking casual style that works in any season, any setting. The leather and waxed canvas upper only looks better as it breaks in. A soft jersey lining and hybrid memory foam footbed keep feet comfortable and reduce fatigue. All set atop a durable rubber outsole.
    Item #503607-A7
    Color:
    $109.00
    $109.00
    Size: Please Select
    • 8
      $109.00
    • 8H
      $109.00
    • 9
      $109.00
    • 9H
      $109.00
    • 10
      $109.00
    • 10H
      $109.00
    • 11
      $109.00
    • 11H
      $109.00
    • 12
      $109.00
    • 13
      $109.00
    Size: Please Select
    • 8
      $109.00
    • 8H
      $109.00
    • 9
      $109.00
    • 9H
      $109.00
    • 10
      $109.00
    • 10H
      $109.00
    • 11
      $109.00
    • 11H
      $109.00
    • 12
      $109.00
    • 13
      $109.00
  • Men's Expedition Nylon Snow Pac Boots

    Men's Expedition Nylon Snow Pac Boots

    Styled after a vintage boot from our archives, the Expedition Nylon Snow Pac Boot combines its retro look with the best of modern winter engineering. 600 grams of Thermolite insulation pairs with sherpa fleece lining to keep your feet warm and comfortable. A deep-treaded rubber outsole adds extra grip, while the waterproof rubber shell helps keeps snow and slush out. There’s no better way to keep your feet warm – and your look on point – this winter.
    Item #503605-A7
    Color:
    $139.00
    $139.00
    Size: Please Select
    • 8
      $139.00
    • 9
      $139.00
    • 10
      $139.00
    • 11
      $139.00
    • 12
      $139.00
    • 13
      $139.00
    Size: Please Select
    • 8
      $139.00
    • 9
      $139.00
    • 10
      $139.00
    • 11
      $139.00
    • 12
      $139.00
    • 13
      $139.00