Marrying a brown long sleeve shirt with khaki chinos is an amazing pick for a laid-back but seriously stylish look. Does this outfit feel too fancy? Let high top sneakers mix things up a bit. A knockout ensemble that will take you from summer to fall like this one makes it super easy to embrace the new season. Guys wondering how to wear cool off-duty outfits as you get into your 30s, this outfit should answer your question.