Once he starts going regularly naked, put underwear on. He'll have a few accidents at first. It took DD a few days, maybe a week, to figure out the underwear thing.
Evan went naked for a few weeks while potty training. We just kept trying underwear at home, and there were plenty of accidents. To keep us from getting too frustrated, if we were having too many accidents, we'd just go back to letting him go naked at home for a few more days. Then we'd try again. For trips outside, I started with really short trips to the grocery store or other places, and I'd put him in two pairs of the padded underwear with a Gerber diaper cover over it. It absorbed enough not to leak, but he could feel that it was wet. We also used a sticker chart, and that seemed to give him some incentive. Eventually, he just got it.
we went from naked to loose shorts with no underware...then big underware(size 4...he's a 3) to reg underware... were having no pee accidents (except in his bathing suit outside after getting out of the pool lol) but he's still figuring out poop...2days accident free though so WHOOOT!
Re: Any suggestions for how to transistion from "naked potty-trained"
Christmas 2011
we went from naked to loose shorts with no underware...then big underware(size 4...he's a 3) to reg underware... were having no pee accidents (except in his bathing suit outside after getting out of the pool lol) but he's still figuring out poop...2days accident free though so WHOOOT!