Men's Comfortable Leather Shoes

A flexible and lightweight black leather dress sneaker with wingtip patterning and Zerogrand technology.

A tan leather wingtip Oxford sneaker with Zerogrand technology for comfort and flexibility.

A brown leather wingtip oxford featuring flexible Zerogrand technology and a cushioned, sneaker-like feel.

A versatile and stylish tan leather plain toe Oxford with memory foam cushioned insoles for all-day comfort.

A comfortable and versatile black leather Oxford shoe with a memory-foam cushioned insole and flexible outsole.

A tan leather golf sneaker with modern performance technology and removable footbeds for customization.

A white leather golf sneaker with modern performance technology and removable footbeds for customization.

A black leather golf sneaker with removable footbeds for custom orthotics or wider feet.

A premium leather sneaker combining classic court style with modern comfort and exceptional cushioning.

A sleek black leather sneaker combining classic style with modern comfort and exceptional cushioning.

A durable brown leather boat shoe with hand-sewn construction and reliable traction for versatile wear.

A refined antique brown leather loafer featuring breathable sock linings and classic moc toe tassel detailing.

A classic black leather cap toe oxford featuring a padded Achilles collar and flexible, cushioned construction.

A classic cordovan burgundy leather oxford featuring a padded Achilles collar and flexible, cushioned construction.

A lightweight leather sneaker featuring laser-cut detailing, GrandPro cushioning, and an ironstone/optic white colorway.

A navy ink nubuck sneaker featuring laser-cut perforations, cushioned insole, and flexible rubber sole for comfort.

A timeless black leather loafer with a full rubber sole and soft leather lining for all-day comfort.

A premium leather loafer in tan and brown, offering all-day comfort with a flexible moccasin construction.

A tan leather wingtip Oxford with memory foam insole and flexible TRUEFOAM outsole for comfort.

A lightweight black leather wingtip Oxford with memory foam cushioning for comfortable support.

A polished black leather cap-toe oxford with fine stitched details and a cushioned memory foam interior.

A comfortable pair of black leather plain toe Oxfords with advanced foot-pampering technology.

A versatile and stylish double monk strap dress shoe in tan/brown leather by Stacy Adams.

A classic tan leather Oxford shoe with a medallion cap-toe design, perfect for special occasions.