Comfortable Wingtip Shoes

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

A flexible and lightweight black leather dress sneaker with wingtip patterning and cushioned comfort.

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

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

A breathable, knit-textile wingtip Oxford with targeted cushioning and ultimate forefoot flexibility in gray.

A modern take on classic wingtip oxfords, featuring airy knit material and memory foam insole for all-day comfort.

A lightweight and flexible navy knit wingtip Oxford that strikes the perfect balance between dressy and casual.

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

A lightweight, flexible wingtip Oxford in black leather with memory foam cushioning for comfort.

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

A modern icon, the Stacy Adams Men's Dunbar Wingtip Oxfords in tan leather, size 11 D-width.

A sustainable, tan leather wingtip oxford sneaker with ornate brogue detailing and a FlowerFoam™ EVA sole.

A modern take on a classic wingtip design, these black leather Oxfords offer all-day comfort.

A tan leather Oxford featuring breathable EnergyWeave uppers and a cushioned sole for all-day comfort.

A sleek black leather cap-toe oxford with memory foam interior for all-day comfort.

A striking two-tone leather wingtip Oxford with brogue detailing, offering comfort and timeless elegance.

A tan leather wingtip Oxford featuring brogue detailing, lightweight cushioning, and a flexible rubber outsole.

A handcrafted tan leather wingtip oxford featuring vegetable-tanned material, cushioned insole, and flexible outsole.

A modern take on the classic wingtip design, the Florsheim Dash Oxford in black is perfect for casual wear.

A timeless wingtip design crafted from full-grain Italian leather with arch-supporting insole and Blake-stitched construction.

A black leather wingtip dress shoe with elastic no-tie laces and a flexible athletic-inspired sole.

A tan leather wingtip Oxford offering timeless elegance and superior cushioning with Grand.OS technology.

A tan nubuck leather wingtip Oxford with intricate brogue detailing for timeless style and comfort.

A tan leather wingtip Oxford featuring brogue detailing and lightweight cushioning for all-day comfort.