820 Brown W
Chicago Shoes is an original handmade shoe brand. Every shoe is sewn by hand on the last, a technique similar to the American-Indian true moccasin construction. The Chicago classic boat shoe is specially designed to fulfill the needs of everybody involved in sea activities, sailing and yachting.
Made by hand with water-resistant leathers and anti-slip, non marking rubber sole the classic boat shoe has an excellent performance on wet and dry surface. True moccasin construction, extra soft anatomic insole, oily treated leathers and padded tongue guarantee comfort, relaxed fitting and flexibility.
In 2025 Chicago shoes will be celebrating 60 years in the field of high-quality leather shoes, but the beginning goes way back. Soon after the Second World War, Nikos, the sixth child of a poor Greek family from Piraeus, decided to emigrate all alone to America to seek his fortune. He went to Chicago because he wanted to be near the water and the boats. In the mornings he searched for work and at night he slept at the big marina, on an abandoned sailboat called “Chicago”.
Oily Treated Leathers
Beautifully resilient. Our leathers are treated for added durability, water resistance, and a ruggedly handsome aesthetic that only gets better with age. This careful treatment process maintains flexibility and enhances each shoe’s character.
Relaxed Fit and Flexibility
Move freely, stay comfortable. Chicago Shoes are constructed for those who prioritize comfort without sacrificing style. A relaxed fit gives you space to breathe, while flexible materials let you move naturally, adapting to every step.
Extra Soft Anatomic Insole
Because comfort is key. The anatomic insole is designed to cradle your foot, relieving pressure and supporting your stride. Made for long days on foot, you’ll experience a cushioned step that adapts to your unique shape.
Water-Resistant
Our shoes are treated with water-resistant finishes to keep you moving, rain or shine. Whether you’re crossing streams, caught in a sudden rain shower, or enjoying coastal activities, our shoes protect and perform.
