Effortlessly blurring the line between cool and relaxed, this pairing of a navy bomber jacket and olive jeans is bound to become your go-to. A good pair of black leather casual boots is an easy way to infuse an added dose of elegance into this look. This one is a savvy option if you're looking for a cool outfit that transitions easily into fall. As a guy in his thirties, you probably want to start dressing like a grown man. In this case, looks like this prove useful as a source of inspo.