Why not reach for a black crew-neck t-shirt and a black windbreaker? As well as super functional, these items look awesome when matched together. Finishing off with casual boots is a fail-safe way to add some extra classiness to this ensemble. So as you can see, it's super easy to look amazing and stay warm when colder weather hits, thanks to this ensemble. As you can see here, as a man in his 40s, you have a wide range of style options.