For a casually dapper look, marry a multi colored plaid long sleeve shirt with a white crew-neck t-shirt — these two pieces play really well together. To give your outfit a classier feel, why not add a pair of beige suede loafers to your look? This combo isn't a hard one to nail and it's summer-appropriate, which is important when it's extremely hot outside. Overall, a smart option if we're talking outfit ideas for 50-something gentlemen.