This ensemble with a bomber jacket and a brown crew-neck sweater isn't so hard to score and is easy to adapt throughout the day. White canvas low top sneakers will add a more laid-back feel to an otherwise classic getup. When you have one of those dreary autumn days, sometimes only a neat getup like this one can get you to face the outside world. Ideal if you're scouting for some incredibly inspiring style for 50-something guys.