Naked bike rides seem OK... They happenall over the country, and most don't seem to cross the lines of their localities' laws.
... But "naked" clothing might be barred. A shirt or even an apron that simulates a nude body may make you persona non grata at the next public event for showing "obscene" material.
Nudist resorts are generally legal on private land. Private events like the nudist "Bare Beach Beer Bash" minimize legal concerns by being hosted by a resort on private land.
The NYPD is OK with bare boobs. The New York Police Department has clarified that officers are not supposed to arrest women simply for being topless in public in the Big Apple (though you may have to be patient with officers who apparently didn't get the memo).
Don't let nude strangers use your pool. This isn't "Lady In the Water," so if a nude woman appears and asks to use your pool, something fishy is probably going on -- like her accomplices robbing you blind while you're distracted.
Don't pose and photograph naked children. While you may be able to convince some that nude photos of your underage children are just family photos from the ol' nudist colony, you aren't likely to succeed if they are in sexually suggestive poses.