For a look that's classy and truly envy-worthy, pair a trenchcoat with a navy vertical striped suit. On the shoe front, go for something on the laid-back end of the spectrum and finish your ensemble with a pair of tobacco chelsea boots. This combination is a viable option if you're crafting a killer getup that transitions easily into fall. So if you're on a mission for outfit inspiration for dressing as you pass the big 5-0, this ensemble is a perfect example.