You won't get in trouble with the law; though you will, as you've experienced, get reactions. Mostly I get a full range of good responses.
Once though some early 20s-something with his buddies -- each in quite long, baggy and billowy board shorts -- gave what he thought was an insulting comment. I was returning to my car after sunning on the beach on Florida's west coast. I was wearing some really comfortable, brief swim trunks, carrying beach towel and a folded beach chair.
He called out to me, "HEY! Where's the rest of it!?!?" (indicating my swim trunks). I smiled, gave an upward nod and continued. Keep on wearing what you find comfortable, man, and don't worry about those without your confidence, ability to break from the pack or other merits.
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