He had clothes in his closet from elementary school. No joke.
I have clothes in my closet from elementary school too. It still fits, it still looks good and I still like it. No problems there 
I think my oldest article of clothing that I still wear on a regular basis is probably from 1991 or 1992.
No, just no

Some of it was an old school uniform. He had a shirt that used to be bright white that was now cream with sweat stains all over the collar. He had this really ugly vest from an 8th grade dance. I have some clothes from high school, but they're in good condition and not hideous. It's not like he's worn any of it in over 10 years, it was just taking up space. He would look at his closet and think "I have clothes, I don't need to go shopping."