You'll be surprised at how super easy it is for any man to get dressed like this. Just a white and red print crew-neck t-shirt and navy jeans. To give your ensemble a classier aesthetic, add a pair of black fringe leather loafers to the equation. This ensemble is basically a lesson in how to dress for boiling hot sunny weather. Gentlemen who are curious how to dress well as you slip into your 50s, you have your answer.