For a casual outfit with a clear fashion twist, you can easily opt for a short sleeve shirt and navy chinos. If in doubt as to what to wear when it comes to footwear, complement your look with light blue low top sneakers. So as you can see, this ensemble is a really savvy option, especially for in-between weather, when the temps are starting to drop. Gentlemen who wonder how to dress well after 30, you have your answer.