If you're scouting for a relaxed and at the same time sharp look, dress in a burgundy crew-neck sweater and black chinos. Our favorite of a myriad of ways to round off this look is with white leather low top sneakers. So as you can see, it's a dapper, not to mention season-appropriate, ensemble to have in your transitional rotation. If you worry about dressing to look more mature, this outfit is a winning option.