Skateboarding in the 60s was a totally freestyle affair, so your fellow skaters wouldn't look down upon you for cruising downhill while sitting on your board, but just like today skating was something you did with friends.
In the spring of '65 photographer Bill Eppridge hung out in New York City and documented all the cool kids on their skateboards, his photos published In the May 14, 1965 issue of Life Magazine.
This was back before skaters surfed pools or grinded rails, a simpler time when they just cruised around and enjoyed the ride, their skateboards seen as a fun but mellow form of mobility rather than a platform for performing stunts.
And even though skateboarding is mostly for young folks there is, was and always will be some older dude hanging around who wants in on the action, only back in the 60s they looked way cooler while not acting their age.
See Stunning Black And White Photos Of Skateboarding In The 1960s here