You'll be amazed at how easy it is for any guy to throw together this casual look. Just a long sleeve shirt paired with grey shorts. When in doubt about what to wear in the shoe department, complete your ensemble with a pair of navy leather slip-on sneakers. What better idea for a summer afternoon? As you're moving through your late 20s, you probably want to start dressing more like a mature gentleman. If that's the case, inspiration like this comes in useful.