This picture is so adorable and funny at the same time and shows a typical look for a young boy growing up in the 60's.
He is complete with his Dennis the Menace haircut. The sides are cut short above the ears and the top is longer and combed forward into long choppy bangs that are completely disheveled. He looks like a little trouble maker with cowboy boots and his straight legged pants don't quite make enough room for those boots. One leg is pushed up for a charmingly childish look. Who has time to worry about how one looks when they are trolling for mischief? His jeans and sweatshirt are light colored and his dark belt isn't quite tucked into a loop.
This picture was taken in 1966 on the sidewalk. What could he be hiding behind his back?
And back then you would have watched a TV show like this on one of these retro televisions with rabbit ears.