Rock and roll and fashion have been closely intertwined since Chuck Berry first strutted across the stage in his wide-lapeled suit and bowtie. Later, as the rollicking 50's rolled into the tumultuous 60's, Elvis's blue suede shoes and Little Richard's candy apple red suits gave way to denim, nehru jackets and, one of the most iconic rock fashion statements, the T-shirt.
There have been many iconic rock shirts — the Rolling Stones' lips created by John Pasche, the CBGBs logo, Joy Division's Unknown Pleasures album cover — but let's talk about shirts actually worn by rock stars. Deborah Harry loved her Vultures Tee, and John Lydon wasn't afraid to self-market PIL. For my money though, it's hard to top the New York City shirt worn by John Lennon captured in the rooftop photo by Bob Gruen. Not only does this improvised photo have Lennon looking cool and still in his prime (age 34), but the T-shirt telegraphs his love of the city he then chose to call home.
To his credit, it was Gruen's vision to put his subject in the $5 shirt he'd just bought off the street. But Lennon's stern pose, unsmiling visage and crossed arms bely a confidence and world-weary attitude that was pure John. From those first clubs in Hamburg to his last days at the Dakota, he was always a tough-minded Liverpool lad with a chip on his shoulder that eventually grew to love humanity. And New York City was proud to include him as one of their own.
For more of the story, check out this 2010 article from New York Magazine by Marc Spitz: http://nymag.com/arts/popmusic/features/69775/