For other celeb-types like Chad Ochocinco and Steve Guttenberg they clearly enjoy jogging in the buff. It got them a lot of media attention which may have been a good thing for their careers...or not.
For the average person, however, who wishes to shed their clothes, keep these ideas in mind:
Don’t even consider jogging without clothes where there may be small children. It won’t matter what time of day you do this, either. If there’s the potential to be seen by minors you may face serious charges such as having to register as a sex offender. This could genuinely ruin your day if you were just doing this for fun.
Wear a backpack so you can put your clothes in it and put them on after your jog. It’s especially important to have quick access to your clothes if you run into trouble.
Jogging in wooded areas or less populated places. It's best to keep from being seen by anyone, including the police.
Keep pepper spray handy and your identification. In the event something happens you want first responders to be able to identify you.
Consider safety in numbers. This is particularly true for women. You never know what kind of creep you’ll come across.
Jogging nude is still pretty crazy to lot of folks. You’re either bold or free spirited or foolish and looking for trouble. To enjoy it, you really want to be both safe and smart. Of course, it’s not likely to catch on in the main stream, but then that’s probably what makes it so much fun to do in the first place!