Make a light blue vertical striped long sleeve shirt and charcoal wool dress pants your outfit choice if you're aiming for a neat, dapper ensemble. Get a little creative when it comes to footwear and play down your outfit with a pair of brown leather brogue boots. Many believe that just because you need to get bundled up you have to sacrifice good style, but that's just not true, and this ensemble is hard proof. This combo proves that even in your fifties your style options are far from limited.