Products

394 products

  • A hand displays the Alden Madison 1272S Chukka Boot in brown Kudu leather with a lug rubber sole, set against a blurred city skyline and bright blue sky.

    Chukka Boot in Kudu Leather 1272S

    $716.00 USD
    $716.00 USD
  • The Alden Madison 1273S - Chukka Boot in Brown Suede, featuring dark stitching and a thick lug rubber sole, rests on weathered wood with a grassy landscape and cloudy sky blurred in the background.

    Chukka Boot in Brown Suede 1273S

    $716.00 USD
    $716.00 USD
  • The Alden Madison 1339 Chukka Boot in Color 8 Shell Cordovan, crafted on the Barrie Last, is shown at an angle on a sunlit curb with blurred trees and greenery in the background.

    Chukka Boot in Color 8 Shell Cordovan 1339

    $1,012.00 USD
    $1,012.00 USD
  • A pair of Alden Madisons 1340 - Chukka Boot in Black Shell Cordovan sits outdoors on dark mulch, with a rusty iron wheel and blurred greenery in the background, enhancing the rustic charm.

    Chukka Boot in Black Shell Cordovan 1340

    $1,010.00 USD
    $1,010.00 USD
  • A single Alden Madison 1340C Chukka Boot in Black Shell Cordovan with laces, polished finish, low heel, Commando Sole, and stitched detailing around the sole is displayed on a white background.

    Chukka Boot with Commando Sole in Black Shell Cordovan 1340C

    $1,030.00 USD
    $1,030.00 USD
  • Alden Madison 13781C Chukka Boot in Brown Chromexcel with black laces, classic Barrie Last, and durable Commando Sole, shown on a metal grate with a blurred background—combining all-day comfort and timeless style.

    Chukka Boot in Brown Chromexcel 13781C

    $778.00 USD
    $778.00 USD
  • A pair of Alden Madison Desert Chukka Boots (model 14580) in tan suede is on an asphalt road. One boot stands, while the other lies on its side, revealing the unique dark crepe sole and textured heel against a blurred street backdrop.

    Desert Chukka Boot in Tan Suede 14580

    $764.00 USD
    $764.00 USD
  • The Alden Madison 1492 - Unlined Chukka in Brown Suede, featuring laces and a Single Flex Leather Sole, is displayed on a weathered wooden surface with an orange wooden wall as the backdrop.

    Unlined Chukka in Brown Suede. 1492

    $730.00 USD
    $730.00 USD
  • An Alden Madison hand holds a pair of 1493 - Unlined Chukka in Snuff Suede boots against a rustic brick wall.

    Unlined Chukka in Snuff Suede 1493

    $730.00 USD
    $730.00 USD
  • The Alden Madison 1494 - Unlined Chukka in Tan Suede features a tan suede upper, brown leather soles on the Leydon last, light-colored laces, visible stitching, and a slightly elevated heel.

    Unlined Chukka in Tan Suede 1494

    $730.00 USD
    $730.00 USD
  • The Alden Madison 1592L Chukka Boot with L3 Sole in Lead Suede, featuring brown laces and a Reverse Antique Welt, sits atop a mossy tree trunk outdoors amid lush green foliage.

    Chukka Boot with L3 Sole in Lead Suede 1592L

    $716.00 USD
    $716.00 USD
  • The Alden Madison 1593L Chukka Boot with L3 Sole in snuff suede sits on a tree stump surrounded by fallen leaves. One boot is upright, and the other showcases its rubber soles patterned grip. Sunlight enhances the textured suede.

    Chukka Boot with L3 Sole in Snuff Suede 1593L

    $716.00 USD
    $716.00 USD
  • The Alden Madison 1655 - Monk Strap Black in Shell Cordovan dress shoe, featuring a silver buckle, rests on a weathered wooden surface with a red wooden wall in the background.

    Monk Strap Black in Shell Cordovan 1655

    $982.00 USD
    $982.00 USD
  • The Alden Madison 1671 - Wing Tip Monk Strap in Color 8 Shell Cordovan showcases a dark brown leather shoe with a decorative buckle and brogue detailing on the toe. It includes a wooden shoe tree and sits elegantly on a white background.
    Sold out

    Wing Tip Monk Strap in Color 8 Shell Cordovan 1671

    $893.00 USD
    $893.00 USD
    Sold out
  • The Alden Madison 17831F - Unlined Leisure Hand Sewn loafer in Brown Chromexcel leather, featuring stitching detail and a classic leather sole, rests on weathered wood amidst green foliage and fallen leaves.

    Unlined Leisure Hand Sewn in Brown Chromexcel 17831F

    $768.00 USD
    $768.00 USD
  • The Alden Madison 21522 - Medallion Cap Toe Blucher Color 8 shoe, featuring a polished reddish-brown leather finish with decorative perforations and a double leather sole, is propped against a concrete wall near a metal door.

    Medallion Cap Toe Blucher Color 8 21522

    $948.00 USD
    $948.00 USD