The Cicero Ave. Single Monk No. 5969 RTW

  • Uppers: Cognac Luxe Calf
  • Burnishing: Light
  • Lining: Brown Calf Leather
  • Buckles: Rounded-Nickel
  • 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

$389.00

Dry Alive Custom Cut Insoles

Step into craftsmanship built for those who value precision in every detail. The Cicero Ave. Single Monk No. 5969 is handcrafted in Spain using time-honored techniques that prioritize durability and refined style in equal measure.

The upper is constructed from Cognac Luxe Calf leather, finished with a light burnishing that adds depth and character without overwhelming the natural grain. This subtle shading ensures each pair develops a unique patina over time, making your shoes distinctly yours with every wear. Inside, a brown calf leather lining provides a smooth, breathable fit that moves with your foot rather than against it, reducing break-in time and increasing all-day comfort.

Rounded-nickel buckles secure the single monk strap with a clean, understated finish that complements the shoe’s overall aesthetic. These aren’t decorative afterthoughts: they’re functional hardware designed to hold their shape and shine through years of use.

The cognac hand-painted leather sole, paired with a rubber component, strikes a practical balance between classic good looks and everyday durability. A black outsole grounds the design, offering traction and grip without sacrificing the shoe’s formal profile. The city welt detailing reinforces the shoe’s structure while adding a visual accent that highlights its construction quality.

Built on the 312 last, this shoe features a rounded toe that nods to traditional English shoemaking. The result is a silhouette that feels classic rather than trend-driven, suited for boardrooms, formal events, or any occasion that calls for understated sophistication.

At the core of this shoe is Blake stitch construction, a method prized for its flexibility and low-profile finish. Unlike bulkier construction techniques, Blake stitching allows the shoe to sit closer to the ground, delivering a sleeker silhouette while still permitting resoling down the line. This means your investment lasts, with the option to restore and refresh the shoe for years to come.

Every element of the Cicero Ave. Single Monk No. 5969 reflects deliberate choices made by skilled artisans. From the leather selection to the final stitch, this shoe is built for those who expect their footwear to perform as well as it looks.

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