Such pieces as a black leather bomber jacket and white chinos are the perfect way to introduce played down dapperness into your off-duty lineup. Put a different spin on this outfit by rounding off with tan suede loafers. When it comes to dressing for weird transition weather, nothing beats a kick-ass ensemble that can take you from season to season. And if we're talking dressing ideas for 50-year-old gentlemen, this ensemble looks nice on most.