You know which kids you can trust and which ones are likely to be in cahoots with each other to pull some sort of prank. It's not a girl who has a crush on you, is it? I use my personality to discourage those. 
If they're used to seeing you in the kilt, then it won't be a surprise to them when you show up kilted. At my school we're "encouraged" to include writing in every class. You might consider having them write a paragraph about why they want you to wear the kilt, and base your actions on their writings. Then, later on, if there are any shenanigans, you'll have some documentation. Keep us posted!
--dbh
When given a choice, most people will choose.
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