Bootleggers

Men

Showing 181–192 of 435 results


  • Our Work socks are crafted with durability and comfort in mind. These socks are designed to withstand the demands of hard work while keeping your feet cozy throughout the day. They are knit with 120 Needles, ensuring a dense, sturdy sock that can endure the rigors of demanding work environments.

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  • The Farm to Feet Timber Light Targeted Cushion 3/4 Crew brings everyday comfort with a touch of nature. Soft, American-grown Merino wool offers natural temperature regulation, moisture management, and odor resistance. Light, targeted cushioning and a seamless toe help prevent rubbing, and gentle compression ensures a secure, stay-put fit from morning to night.

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    • These Feetures® High Performance Cushion No Show Tab socks are a classic design that are engineered for high impact activities so you can push your workout that extra distance!
    • No-show cut keeps your socks just out of sight and your feet feeling dry and comfy.
    • Sold as one-pair pack.
    • Power bands of Lycra, designed to contour to each individual foot, lead to an enhanced fit, which reduces movement to avoid blisters.
    • iWick® synthetic fibers wick moisture to keep feet cool and dry.
    • Y-heel design prevents the sock from sliding into the shoe.
    • The Perfect Toe® seamless toe eliminates any irritating toe seams.
    • 200 Needle construction utilizes enhanced knitting techniques for increased comfort and durability.
    • High density cushioning adds extra protection in high impact areas.
    • 79% polyester, 18% nylon, 3% spandex.
    • Machine wash, hang dry.
    • Imported.
    Select options This product has multiple variants. The options may be chosen on the product page
    • These Feetures® High Performance Cushion No Show Tab socks are a classic design that are engineered for high impact activities so you can push your workout that extra distance!
    • No-show cut keeps your socks just out of sight and your feet feeling dry and comfy.
    • Sold as one-pair pack.
    • Power bands of Lycra, designed to contour to each individual foot, lead to an enhanced fit, which reduces movement to avoid blisters.
    • iWick® synthetic fibers wick moisture to keep feet cool and dry.
    • Y-heel design prevents the sock from sliding into the shoe.
    • The Perfect Toe® seamless toe eliminates any irritating toe seams.
    • 200 Needle construction utilizes enhanced knitting techniques for increased comfort and durability.
    • High density cushioning adds extra protection in high impact areas.
    • 79% polyester, 18% nylon, 3% spandex.
    • Machine wash, hang dry.
    • Imported.
    Select options This product has multiple variants. The options may be chosen on the product page
    • The professional Florsheim® Midtown Cap Toe Oxford makes any work attire look perfectly polished.
    • Full-grain leather uppers with a cap toe.
    • Traditional lace-up closure.
    • Breathable and moisture-wicking Suedetec synthetic linings. Removable footbed is generously cushioned and features OrthoLite® high rebound foam for maximum support.
    • Flexible rubber outsole.
    • Imported.
    Select options This product has multiple variants. The options may be chosen on the product page
    • The professional Florsheim® Midtown Cap Toe Oxford makes any work attire look perfectly polished.
    • Full-grain leather uppers with a cap toe.
    • Traditional lace-up closure.
    • Breathable and moisture-wicking Suedetec synthetic linings. Removable footbed is generously cushioned and features OrthoLite® high rebound foam for maximum support.
    • Flexible rubber outsole.
    • Imported.
    Select options This product has multiple variants. The options may be chosen on the product page
    • Make a clean style statement with the spruce Florsheim® Norwalk Plain Toe Oxford, a leather wingtip oxford with closed lacing atop a sporty-looking man-made rubber sole.
    • Lace-up leather loafer with rounded toe features soft textile lining and a removable comfort footbed for the best underfoot cushioning.
    • Textured man-made rubber outsole with low block heel.
    • Imported.
    Select options This product has multiple variants. The options may be chosen on the product page
  • Purchase a Bootlegger’s Gift Card today. Any amount available with a $25 minimum. Cards do not expire and there are no fees.

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  • The HOKA Men’s Arahi SR Shoes bring stability, comfort, and workplace-ready performance together in one dependable design. The shoe provides a smooth ride inspired by the original Arahi while adding a slip-resistant outsole built for demanding environments. A breathable mesh upper helps keep feet cool, and a water repellant coating adds protection for splash-prone settings. The enhanced H Frame offers reliable stability without compromising natural movement. Finished with an easy step in heel that flexes and springs back into place, the Arahi SR makes getting in and out effortless during busy days on the job

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  • One of the hardest working shoes in the HOKA lineup, the Bondi 9 delivers peak plushness for everyday miles. Overhauled from top to bottom, we’ve increased the stack height and added a new premium foam midsole to deliver that soft, resilient ride that’s become synonymous with the Bondi.

    Select options This product has multiple variants. The options may be chosen on the product page
  • One of the hardest working shoes in the HOKA lineup, the Bondi 9 delivers peak plushness for everyday miles. Overhauled from top to bottom, we’ve increased the stack height and added a new premium foam midsole to deliver that soft, resilient ride that’s become synonymous with the Bondi. Elevated with a 3D molded collar and structured knit upper with zonal breathability, this ultra-cushioned cult favorite has been finished with Durabrasion rubber to combat high wear zones.

    Select options This product has multiple variants. The options may be chosen on the product page
  • Rain or shine. Street to summit.

    Built at the intersection of road and trail, the Challenger 7 GTX has been completely reimagined from the ground up. Combining a simplified mesh upper with a soft new foam, we’ve increased the stack height for a plusher feel and added GORE-TEX INVISIBLE FIT with recycled content product technology for enhanced protection in inclement weather. Inspired by gravel tires, we’ve cued up smaller, tightly spaced lugs in center and larger, more aggressive lugs at the perimeter designed for improved traction on uneven terrain.
    Sale!
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