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Ankle Boots For Men

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  1. Addison Lug Lace Up
    WATERPROOF

    Addison Lug Lace Up

    $458.00

    …heirloom heritage-inspired Addison boots are Made in the USA and are constructed from smooth pull up waterproof leather affixed to a firm lug sole. A failsafe footwear option for traversing city and off-road terrain, they feature a smart lace-up closure and Goodyear welting for effortless dressing.

    Related Products Addison | Waterproof | Men's Lug
  2. Weston Harness

    $398.00 $279.00

    A clean-cut classic with Harness styling. Embellished with our distinctive studs and ring, a chiseled snub toe and polished leather outsoles, this back-zip dress boot in heavily oiled and vegetable tanned full grain Italian leather is refined yet always ready for adventure.

    Related Products Weston | Harness | Weston Harness
  3. Prison Boot

    $378.00 $279.00 - $378.00

    …to last, the Prison Boot features a tough rubber outsole and thick leather laces. Tumbled with stones for a beat-up look, these boots are the same as those made for the Arkansas Prison system and even feature a prison number stamped on the heel. We are not responsible for any rules you break while…

    Related Products Prison Boot | Prison | Arkansas
  4. Prison Boot

    $378.00 $279.00 - $378.00

    …Prison boots are Made in the USA from a heavily burnished Italian leather that only gets better with each and every wear. The “prison number” stamped on the heel is a design detail inspired by prison serial numbers- the accent further enhances the brands characteristic trait for fusing together…

    Related Products Prison Boot | Prison | Men's Prison Boots
  5. Prison Boot

    $378.00

    These lace-up Prison boots are Made in the USA from a combination of waxed suede and Horween leather that has been treated with a special hand-finish that only gets better with each and every wear. The “prison number” stamped on the heel is a design detail inspired by prison serial numbers- the…

    Related Products Prison | Prison Boot | Men's Prison Boots
  6. Officer Cuff Boot

    $428.00

    These military-inspired lace-up boots emanate quality craftsmanship in a stonewashed leather. The removable cuff feature re-appropriates this style for versatile urban-wear. High-traction full rubber sole and Goodyear welted construction means they are built to ensure lasting comfort. Inside zip…

    Related Products Officer | Zip | Mens Boots
  7. Jacob Engineer

    $378.00

    A classic engineer boot streamlined for modern city slickers. Beautifully handcrafted from suede and oiled just so, this boot looks better and better the more it’s worn. Buckle straps at the ankle and above, so it's time to get moving.

    Related Products Jacob Engineer | Jacob | Suede
  8. Jacob Engineer

    $378.00 $279.00 - $378.00

    A classic engineer boot streamlined for modern city slickers. Beautifully handcrafted with antiqued full grain leather and buckle straps at the ankle and above. Polished just so, this boot looks better and better the more it’s worn. Get moving.

    Related Products Engineer | Jacob Engineer | Jacob
  9. Sam Lace Up

    $278.00 $229.00

    Driving classic cars or grabbing coffee in the morning, this is the perfect everyday ankle boot. The suede is tanned for weeks to create a deep and vibrantly luxurious hand feel. Soft and supple, the suede literally molds to your foot and ankle.

    Related Products Sam Lace Up | Suede | Sam
  10. Woodson Hiker

    $378.00

    Designed for backpacking and big city adventures. In tumbled leather that’s vegetable-tanned, this lightweight hiking boot offers color, ease and comfort. Outsole pops against upper for a touch of contrast; thick, padded collar cradles the ankle with support; speed hooks get you easily in and out.

    Related Products Woodson Hiker
  11. Woodson Hiker

    $378.00

    Designed for backpacking and big city adventures. In brush off full grain leather, this lightweight hiking boot offers color, ease and comfort: Outsole pops against upper for a touch of contrast; thick, padded collar cradles the ankle with support; speed hooks get you easily in and out.

    Related Products Hiker | Woodson | Woodson Hiker
  12. Jacob Engineer

    $378.00

    A classic engineer boot streamlined for modern city slickers. Beautifully handcrafted from leather and vegetable crusted just so, this boot looks better and better the more it’s worn. Buckle straps at the ankle and above, so it's time to get moving.

    Related Products Jacob Engineer | Engineer | Jacob