I recently hooped naked for the first time. I was hanging out at Baker Beach with some friends and some hoops, and since Baker Beach is a nude beach it made sense for us to hoop naked.
Besides the obvious feelings of freedom and unrestraint, naked hooping brings with it another benefit: the traction of the skin. When hooping with my knees, I was never very good at pushing the hoop back up to my hips with my thighs. But the traction of my naked skin made it very easy for me to wiggle the hoop up from my knees.
After the naked hooping practice it has been much easier for me to bring the hoop up from my knees, even with clothes on. The nudity has served as my training wheels.