What a great photo. It has a 1950s vibe to it, but, since traffic going through Washington Square ended in 1958/1959, it is likely early 1960s. Notice the sign stating Do Not Enter in the middle of the Arch so there was still the threat – hence the warning. The street sign Washington Sq N/5th Av is pretty great also. And it was a bus stop too! Fashion wise, men and women are still wearing hats here. It always amazes me how quickly hats phased out once the “hippie” era of the 60s took root; the styles changed so dramatically. Women were wearing gloves at this point too – but everything soon shifted.
Source: When Downtown was Cool, Daily Beast, April 10, 2014
Previously at Washington Square Park Blog: