Here’s an Out Our Way (by J. R. Williams) cartoon from August 5, 1964. Most of these strips in the 1960s, as far as I can tell, are repeats from the 1940s or so, so I suspect it’s really from sometime around then.
Out Our Way, August 5, 1964
Regardless, it hearkens back to a time when not only did kids normally go barefoot for the summer, they were actively subversive in doing so. Nowadays, so many don’t seem to have a clue in that regard.
Ahcuah 
And I wonder why one ever had to be subversive about it. Shouldn’t this mother be glad that the shoes and socks wear out less? Some parents …
(The good thing about feet: Walking doesn’t wear them out but makes them stronger!)
Lest other parents and neighbors should think that the child is poor or not well cared for. People are ready to sacrifice so much for the looks!
With all the best intentions for their child, of course …