Pair a navy plaid wool blazer with charcoal skinny jeans for a casual getup with a clear fashion twist. Dial up the wow factor of your outfit with dark brown leather double monks. So if you're on the hunt for an ensemble that's dapper but also feels totally season-appropriate, this one fits the task well. As you're maturing from your 20s to your 30s, you probably want to start dressing more like a mature gentleman. In this case, combinations like this become a great source of inspo.