When the setting calls for an effortlessly neat menswear style, rock a navy nylon shirt jacket with white chinos. In the shoe department, go for something on the smarter end of the spectrum by finishing with burgundy leather tassel loafers. It's is a good pick when it comes to a neat ensemble that transitions easily into fall. Wondering how to dress appropriately for your age as you slip into your 50s? This pairing is a perfect example.