Those people are/were young, so what the heck ! Sunglasses indoors or after dark I've always thought of as over the top ( some of my mates wore them onstage mind you, although most certainly not whilst being in a band with me ) but the sockless look within this context is great I think.....

I think he looks great, but I would feel too self conscious with sunglasses inside and pants that short (they are almost capri length). I do like the overall feeling of it though, especially the guy in sneakers.

The varying pant length on old pics like these: overall short, but with quite a bit of tolerance. Like you said ISR, it seems less self-conscious than most of us are going at it. I like to think that the leg stops just below the ankle, the pants stop where the feet start.  These guys were just wearing a pair of pants as long as they weren't long.

I love the loafers with no socks look.  Not sure if I would feel comfortable going sockless to the office, but so in more casual situations.