School I went to actually had in the dress code that cheerleaders weren't allowed to wear their outfits in school, because the top and the skirts violated the general dress code.
I always challenged the boundaries of their dress code.
They had a rule saying people couldn't wear NASCAR jackets because they had "Winston" and "Bud" decals on them. So, I bought a Kevin Harvick GM Goodwreck jacket (in the NEXTEL Cup era) and it didn't have the "Bud Pole Award" patch on it at all and wore it. Got sent to the principal's office and asked them to show me where the Bud and Winston patches were.
Another time, I had a Mark Martin shirt on. This was when he was driving the Viagra car.
So, an administrator walks up to me and says, "You can't wear that shirt, it's promoting sexuality". I reply, "Viagra's a pill". Dude followed up by saying I probably don't watch NASCAR and don't like Mark Martin and was just wearing it to challenge their authority.