This summer let the trilby protect your face from the sun with the added appeal of a dandified look. Trilby hats are du jour and are worn by almost every age bracket. For men over 40 you do not want to be caught wearing a trucker hat, cos it might send a msg across(i'm a slob).
The good thing about Trilby hats is that they can be dressed down or amped up to suit whatever occasion. They look good with a dress shirt or a t-shirt,jeans or Khaki. Footwear could be sneakers or dress shoes, but i'd go with a hybrid.