2. Wanny Di Filippo
The most colorful man in Milan is Wanny Di Filippo, also known as Crisp Kringle. The man has gained a dedicated following for his vibrant style that mashes together patterns and textures into a style that is instantly recognizable and unique. The dude behind one of Italy's most revered leather goods manufacturers, Il Bisonte, is a street style magnet for his outfits that clearly and proudly say, "I simply do not give a fuck" and is an example of how we should dress and live in our golden years.