Certain decades were just cooler than others. The 1920s rocked; the 30s … not so much. The 50s were a bit of a red scare, the 60s were all about rock n’ roll and free love – and the Cold War still, too. Often the easiest way to pinpoint a “cool” decade is to take a look at the sartorial trends popular with the young folk. For example: Those roaring twenties had the liberated flapper girls in slinky dresses and hip hats. The 50s saw more short sleeved button-down shirts tucked into starched blue jeans. Not as hip. But not as bad as in the 1980s, when things just went off the rails entirely.