To look like a true gent at all times, try teaming a brown plaid blazer with grey dress pants. Our favorite of an endless number of ways to finish this ensemble is with a pair of dark brown leather chelsea boots. When it's one of those gloomy fall days, sometimes only a killer outfit like this one can get you out the door in the morning. So if you're scouting for a stylish and age-appropriate pairing, this one fits the bill.