The Madison St. Chukka Boot No. 5932 RTW

  • Uppers: Light Brown Luxe Calf
  • Lining: Brown Calf Leather
  • Laces: Flat-Brown
  • Sole: Cognac Hand-Painted Leather w/Rubber
  • Outsole: Black
  • City Welt
  • Last: The 312 – Featuring a Rounded Toe for a Traditional English Style
  • Blake Stitch Construction

Handcrafted in Spain

  • Lace-ups, boots, and sneakers tend to fit true to size.
  • Loafers, Belgian slippers, boat shoes, and drivers tend to run a 1/2 size small.
  • If you are between sizes, order the larger size and request our custom insoles
  • Don’t forget to try the FeetSizer App!

More Information Available Here

$399.00

Dry Alive Custom Cut Insoles

Step into refined craftsmanship with the Madison St. Chukka Boot, a style built for those who value quality without excess. Every detail serves a purpose, from the boot’s construction to the materials chosen to make it last.

The uppers are made from Light Brown Luxe Calf leather, prized for its soft hand-feel and rich texture that only improves with wear. Inside, a full Brown Calf leather lining keeps your foot comfortable through long days, molding to your foot over time for a fit that feels custom-made. Flat brown laces complete the look with understated sophistication.

The sole tells its own story. Hand-painted in a warm Cognac tone and paired with a durable rubber base, it delivers both striking visual depth and reliable traction underfoot. A black outsole grounds the design, adding contrast without competing for attention. The City Welt detailing reinforces the boot’s structure, ensuring it holds its shape through years of use.

Built on the 312 Last, the Madison St. Chukka features a rounded toe that nods to traditional English shoemaking. This shape offers a classic silhouette that pairs as easily with tailored trousers as it does with raw denim. It’s a versatile design, equally suited for the office or a weekend outing.

Underneath the polish is a Blake Stitch Construction, a technique that keeps the boot sleek and low-profile while allowing for future resoling. This method, favored by shoemakers for its clean lines and lightweight feel, means you can keep wearing (and re-wearing) this boot for years.

Every pair is handcrafted in Spain by skilled artisans who understand the value of precision. From cutting the leather to stitching the final seam, the process reflects decades of shoemaking expertise passed down through generations.

The Madison St. Chukka Boot No. 5932 RTW isn’t just footwear—it’s a long-term investment in quality, comfort, and timeless style. Built to perform and designed to last, this boot earns its place in any wardrobe built on substance over trend.

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