This laid-back pairing of a trenchcoat and a dark brown track suit is a real life saver when you need to look casual and cool in a flash. To add a bit of fanciness to this outfit, add tan casual boots to the mix. If it's one of those dreary fall days, what better to brighten things up than a dapper look like this one? As a 30-something Millennial man, you probably want to start dressing like an adult. That's when inspiration like this comes in very handy.