You're looking at the definitive proof that a grey overcoat and grey dress pants look amazing when teamed together in a classy look for today's guy. A pair of chelsea boots will add edginess to this outfit. Can you see how super easy it is to look stylish and stay warm when chillier weather hits, all thanks to outfits like this one? When it comes to style tips for middle-aged men, this combo looks good on almost any gent.