Marrying a light blue plaid blazer and a white dress shirt is a guaranteed way to inject your closet with some manly refinement. If you want to easily step up your outfit with footwear, add dark brown leather loafers to the equation. When you're having one of those dull fall days, sometimes only a kick-ass look like this one can get you out the door in the morning. Wondering how you should dress as you age into your 50s? This combo is a vivid example.