Cole Haan LunarGrand Wingtip

They don't look quite like typical wing tips, but if it weren't for their colorful outsoles, you'd be hard pressed to tell the difference. Unless, of course, you're wearing them. Designed to tackle the tough streets of NYC, the Cole Haan LunarGrand Wingtip ($250) weds Nike's ultra-lightweight Lunarlon cushioning system to a classic Cole Haan last with leather welt details and premium suede uppers to create a dress show for those who consider jeans, a button down, and a jacket to be way dressy. Other features include a wider forefoot, slimmer rounded toe, partial lining, and a micro-diamond tread texture on the bottom for maximum traction.

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