I used to have this ironclad rule about the condition my kids' clothes should be in before they're allowed to leave the house. "Nothing dirty, nothing torn." 
The "dirty" part went out the window when my older son joined the stage crew and started volunteering for Habitat for Humanity. Both of these projects involved paint, which seems to have a magnetic attraction to clothing. So he kept a couple of paint-spattered T-shirts and pairs of now-colorful jeans, using those when he had stage crew work to do. I have had to remind him that he shouldn't wear his "paint jeans" when he wants to look nice.
My daughter has been on the stage crew as well, and she ruined the jacket from her field hockey warm-up suit (cost: $75) with paint within a week of receiving it. And her new favorite jeans are a pair of those pre-ruined distressed denims with large holes all over them.
She has the best timing; she chooses to wear those jeans on the coldest days of the year. Not only that, but she decides that those cold days would be good days to meet a bunch of her friends at the pizza shop 1/2 mile away. She walks there, in those ripped jeans. I've offered to give her a ride so she doesn't have to walk in the cold, but she never takes me up on it. I'm convinced that one of these days I'm going to have to take her to the doctor because she's got frostbite in the spots where the jeans are ripped.
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