So as you can see, it doesn't require that much effort for a man to look effortlessly classic. Wear a sweater vest with a charcoal long sleeve shirt and be sure you'll look incredibly stylish. Why not take a more laid-back approach with shoes and complement your outfit with black leather casual boots? As you can see here, it's very easy to look amazing and stay warm when cooler weather hits, all thanks to combinations like this one. This ensemble demonstrates how to keep killing it in casual dressing as a man in his 30s.