If you're all about relaxed dressing when it comes to fashion, you'll appreciate this street style combination of a charcoal crew-neck t-shirt and grey skinny jeans. White low top sneakers are a simple way to add a confident kick to the look. As the weather gets warmer, it's time to shed those bulky winter gear and choose an outfit that's lighter, like this one here. When it comes to casual dressing ideas for 50-something men, this look is ideal.