Wingtips have always been on the casual side of the dress shoe spectrum, but footwear legend Allen Edmonds has nudged the style into more aggressive territory with their Special Edition Kasmuk ($300). The striking blue denim uppers are definitely a step outside of the company’s typical brogue comfort zone. Their risk, however, is your fashionable reward. We see these shoes as versatile wardrobe addition that can move seamlessly between jeans, light colored chinos or other casual pants. Order this web-only edition before June 3 and they’ll even waive the custom fee. Reward indeed.