At times, the point of vintage or retro clothing is to show how clever your fashion sense is, but when everyone is referencing the same thing, it becomes monotonous and played out. If everyone draws back to the same point in history, then it's no longer worth referencing. Find moments that are unique to yourself and the place you grew up, or what you have a keen interest in. When you break out the vintage shirt because it was made in your hometown, you'll feel that much more of a truthful connection.