Theres something to be said about longboarding barefoot. In my eyes, its a bit of a controversial subject. On one hand, it can be viewed as incredibly unsafe. And for good reason. In some situations, the most logical way to slow down is by dragging your foot on the ground. On the other hand, however, it is an extremely liberating activity.
The increased feeling between the board and the bottoms of your feet. Feeling the vibrations picked up from the asphalt, dampened by your wheels, bushing, and flex. I don't know, maybe its just me, but I think it's great.
Of course, I do not do anything like the video that I linked above (Striker is insane). I'll cruise. At speeds as fast as I'm comfortable going. I definitely skate way more cautiously without shoes on so that if something were to take me by surprise, I'd be able to react to it without getting hurt.
I think the best is skating barefoot in the rain. The first time I did it was simply because I was coming home from a late class, it was raining, and I didn't feel like getting my shoes and socks wet. Talk about a tactile revelation. I was hooked. And now, since I prefer to go barefoot on most occasions anyway, it just makes sense to longboard barefoot from time to time. Know what I'm saying?
Anyways, give it a try. And don't bash it till you try it. Hopefully you'll get the same sort of experience out of it that I do.