As you can see, it doesn't require that much effort for a man to look dapper. Wear a navy crew-neck t-shirt and olive dress pants and you'll look incredibly stylish. A pair of tobacco suede chelsea boots will add a different twist to your getup. Come hot summer days you want to feel cool and sharp –– this getup is just the one you need. Men who are curious how to dress fashionably well into your 50s, you have your answer.