You'll be amazed at how easy it is for any gentleman to get dressed this way. Just a tobacco shirt jacket matched with a black turtleneck. Complement this ensemble with a pair of black leather chelsea boots to easily boost the wow factor of this look. As you can see, it's extremely easy to look stylish and stay warm when chillier weather arrives, all thanks to ensembles like this. This pairing demonstrates that figuring out how to dress well over 30 is not that daunting a task.