We're loving how this combo of a charcoal wool double breasted blazer and a light blue dress shirt immediately makes any man look classy and stylish. Bring a playful touch to your ensemble by finishing with dark brown fringe leather loafers. So as you can see, it's super easy to look stylish and stay comfortable come chillier weather, all thanks to ensembles like this. So if you're scouting for fashion tips on what to wear as you slip into your 50s, this combination is a wonderful example.