A burgundy cardigan and a light blue gingham long sleeve shirt will inject your current lineup this casually dapper vibe. Tap into some David Beckham stylishness and class up your look with dark brown leather chelsea boots. As you can see here, this ensemble is a really savvy pick, especially for weird transition weather, when the mercury is starting to drop. And if we're talking casual dressing ideas for guys in their fifties, this combination looks good on most guys.