A long sleeve t-shirt and charcoal dress pants are a great pairing that will get you the proper amount of attention. Infuse a more relaxed vibe into your outfit by wearing a pair of black leather casual boots. Can you see how extremely easy it is to look stylish and stay snug when cooler days are here, thanks to this ensemble? And if we're talking dressing ideas for 50-year-old gents, this combination is ideal.