Braid your hair the night before. Don't wash it. Take it out and shake your mane like you just don't care!
Find an over-sized shirt. Plaid is king. Wear any pants you want, preferably just out of the hamper. If it still looks too crisp, crumple your clothes into a ball and stand on them while you brush your teeth.
Before you leave your house, just grab a hoodie to tie around your waist and some old tennis-shoes or thick-soled clunkers.
It's '90s grunge, baby.
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