This combination of a black double breasted blazer and blue wool dress pants can only be described as ridiculously dapper and sophisticated. Chelsea boots will give a mellow feel to an otherwise dressy getup. As you can see here, it's super easy to look seriously stylish and stay cozy when cooler days are here, all thanks to outfits like this one. And if we're talking style for over-50 guys, this combination looks cool on almost anyone.