My thoughts on trucker hats and all other fashion intentionally ugly, retrogusting, and ironic:

When it comes right down to it, this kind of styling is just a contest to see who can pull off the most heinous clothing by sheer force of their conceit. Goal: to be the one looking the worst with the most attitude. It’s a test of wills; a confidence contest. If you can keep your cool while wearing something as ugly as a trucker hat, coulots, or fanny pack, then you really must be confident.

…Or else just take yourself way too seriously.