Go for a simple yet seriously stylish option by opting for a brown gingham blazer and a light blue vertical striped dress shirt. You could perhaps get a bit experimental in the footwear department and add dark brown leather chelsea boots to the equation. This outfit is perfect for summer-to-fall weather. As a 30-something Millennial gentleman, you probably want to start dressing more professionally. If that's the case, combinations like this prove useful as a source of inspiration.