For more than 80 years, shoemaker Cole Haan has been a standard-bearer of fine footwear – and the go-to source for the peerless business wingtip. The Air Madison Wingtip Oxford continues the tradition: Crafted from hand-burnished calfskin, the oxford sits sleekly atop a leather stacked heel and grooved sole for better traction. But what really sets the shoe apart is its Nike Air technology hidden deep within the sole. The tech – from Cole Haan's parent company – is engineered to provide sneaker-like cushioning throughout the day, resulting in a shoe that's fit for both work and play, suit and denim, and all-day meetings and long city walks alike. You can't go wrong with the classic black or tan, but for a summer shoe, we'd opt to go bolder and brighter with the charcoal colorway with lavender-hued laces. [$248;]