This is undeniable proof that a black turtleneck and charcoal plaid chinos are awesome when worn together in a laid-back look. To add a bit of flair to this ensemble, complement this outfit with tobacco leather loafers. Can you see how very easy it is to look stylish and stay comfy when cooler weather hits, thanks to this outfit? When it comes to style for guys in their 50s, this outfit looks great on almost any gentleman.