The Chicago is a close cousin to our popular Maine loafer, designed in response to customer feedback for a penny loafer with a round toe box similar to our Connor tassel loafers. Made from premium Museum Calf leather from the Ilcea Tannery, this style combines elegance and comfort.

GOODYEAR FLEX COLLECTION

Our GYFlex collection offers the same exceptional craftsmanship as our other footwear, with one key improvement: enhanced comfort.

Each pair features a rubber sole and is stitched without a metal shank, allowing for maximum flexibility. This means a shorter break-in period, shoes that conform more easily to your walking style, and increased overall comfort.

This style runs large. Pick one size smaller than your usual when ordering. .