I'm pretty confident this happened in 6th grade. Back in 6th grade we had a class called "cycle" where we would rotate an elective course every 6 weeks. If I remember correctly (and I can't believe this was in 1989, by the way) we would take Spanish, French, Latin, Health, Computers, and a Music cycle.
Anyway, back before I was the fashion maven I am today, I could not have cared less about fashion. In elementary school Notorious and I essentially had contests over who could come up with the best combination of sweatpants and t-shirts. In order to win the contest you had to have the brightest sweatpants and the best pop culture reference on your t-shirt. Matching or coordinating the colors did not make a difference. For example, I would win on the days when I would wear my bright orange sweatpants along with my "avoid the noid" t-shirt. As Diesal will tell you (whenever you're making fun of him and he wants to deflect the attention away from himself) I didn't even own a pair of jeans until 7th grade. I was generally sweatpants all the way through then, although I did have some of those interesting Bugle Boy pants with the zippers and stuff all over them '80s style.
So this happened in 6th grade, during middle school, but before I decided to actually put any thought into my outfits aside from which company's witty t-shirt expressed my mood that day. If I'm remembering correctly on that day I was wearing cargo sweatpants (because really I was just way ahead of my time, rather than a fashion misfit) and a t-shirt that said PennState-asaurus (do you remember those -asaurus t-shirts? Those were weird.) that was most likely an XL size even though I think I was 5'1" at the time. The shirt came down to my knees, which for some reason was also fashionable back then, or else I was just a huge dork. Probably both.
Here's the actual story. This is one of LJT's favorites, so I hope he will add or amend the story as necessary. We were in the music cycle and in the music room with Mr. Streckfuss. This was before he nearly killed our bass drummer for playing the song incorrectly. And also this was just a introduction to music class, so he couldn't be all that mean. I had taken my 3 years of piano lessons and so when he asked if someone could play some notes on the piano in order for him to demonstrate something or another, I volunteered.
So I'm wearing my cargo sweatpants, and my shirt that comes down to my knees, and I had been sitting, and most likely fidgeting in this chair for a while now. I get up to walk to the piano and wouldn't you know it, the now famous mother of all embarrassment, the shirt wedgie. I had a wedgie so big, that not only my underwear, not only my sweatpants, but also my XL t-shirt had jammed its way all up into my buttcrack. All I really remember is the 6th grade Notorious LJT, who was only slightly more uncouth than he is now and who had been sitting next to me, laughing hysterically as I tried to play off the nonchalant wedgie pull as I walked to the piano. I like to think that I redeemed myself by playing the notes on the piano correctly, but in retrospect, that probably just made me look like an even bigger nerd.
It was awesome.