Effortlessly blurring the line between dapper and laid-back, this pairing of a red and navy long sleeve shirt and a burgundy plaid long sleeve shirt can easily become one of your go-tos. For something more on the sophisticated end to round off your getup, complement this outfit with brown leather loafers. This combination is an appealing choice when it comes to a killer outfit that transitions easily into fall. This outfit looks cool no matter what age you are.