Swim trunks

You will start with a piece of clothing that very easy to lose and if you get a lot of backlash it's easy to explain it as an accident: swim trunks.

You go to your dresser and find a pair you don't mind losing forever. You make sure not to tie the drawstring. You think about just removing it entirely, but on the off chance that someone finds your swim trunks, you don't want them to discover you sabotaged them. This might just be paranoia and your previous lack of freedom making you overthink things, but functionally, it won't make a difference in being able to get yourself naked.

There's a public pool nearby, a water park and a beach. Where do you go to lose your trunks?