Finding the right mix of upscale style and casual materials can be tough when producing a quasi-dress shoe, but the Mark McNairy New Amsterdam Longwing ($350) has it more or less nailed. Featuring a grey suede upper, perforated wing-tip details, corded laces, a comfy, supportive footbed, and an oversized welted EVA sole, just in case you need a half-inch boost when heading out on the town.