For me, it was probably last winter, almost a year ago, when I spent my winter break in Australia–at one point, I was in sunny Queensland and all I had to do was swim and walk along the beaches for about a week. Either that, or the time I came down with an infected kidney and I was in a hospital with a terrible high fever for a week or so–I don’t remember that so well (sophomore year of college), but I can’t imagine that my feet felt chilly when I was running that fever, so I was probably barefoot the whole time.
During my freshman year of college I often wore sandals without socks on school days. I can’t give a precise number of consecutive days, but it wouldn’t surprise me to learn that I went a week without socks.
I am a sockaholic. I wear mine all the time, even in the summer. I have permanantly white feet and a tan line at my ankles that rarely fades. If I do wear shoes without socks, you really can’t even tell. It isn’t pretty.
It is very cold in WI half of the year, so going barefoot isn’t always the best. But I don’t know why I still wear socks in the summer. I guess I just don’t like the sweaty-feet-inside-of-shoes feeling.
When I was a kid I spent every summer barefoot. I am not sure when it changed. College maybe.
For some reason I can’t even begin to fathom nearly 40 years later, I wore moccasins without socks for most of the time I was in college - including Cambridge MA winters.
As for Sox, being a Yankee fan I’ve done without them forever.
I pretty much did two years in Peace Corps Cameroon without socks- the longest stretch was maybe a year. It was unholy hot (more than 100 most days) and local custom meant I had to wear skirts. So I just wore nice sandals all the time.