Skip to main content

Shoes made for

comfort style adventure durability for you.

Featured Shoes

Move freely, stay comfortable

Quality Over Quantity

Unleash Your Spirit. Explore with Chicago Shoes

1

Water-Resistant

Leathers 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 sea and coastal activities, our shoes protect and perform.
2

American-Indian True Moccasin Construction

Inspired by tradition, crafted with precision. Chicago Shoes employs a moccasin structure, where the leather wraps around the foot for a naturally comfortable, fitted experience that molds perfectly to your feet over time.
3

Anti-Slip Non-Marking Rubber Sole

Grip without the slip. For wet or slippery surfaces, the anti-slip technology in our non-marking rubber soles ensures you have reliable traction without scuffing or marking up delicate surfaces or boat decks.
4

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.
5

Oily Treated Leathers

Beautifully resilient. The leathers we use are treated with special oils 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.
6

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.

The real story of CHICAGO SHOES

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 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 loved water and sailing. In the mornings he searched for work and at night he slept at the big marina, on an abandoned sailboat named “Chicago”.

A bit later Nikos found a job in a small shoe factory and he met Nikolas, another young Greek immigrant who worked at the marina taking care of the “Chicago” boat whose owner was very rich, but old and sick

The old American boat owner died soon and left in his will the boat to the two Greek boys. Nikolas and Nikos sold the boat, packed their few belongings and returned to Greece to restart their lives. They stayed with Nikos’s family and found work in a small shoe factory close by.

water-resistant leathers oily treated, handmade, anti-slip, non marking rubber sole, extra soft anatomic insole

Our Commitment to Sustainability

At Chicago Shoes, we don’t just care about where you’re going; we care about where our materials come from. Our commitment to sustainable sourcing, ethical labor practices, and eco-friendly manufacturing ensures that every pair of shoes supports both your feet and the environment. By choosing Chicago Shoes, you’re choosing products that are crafted to last, reducing waste and investing in quality over quantity.