Most recent, but not the absolute worst, was ripping my pants at work. I bent down to pick something up and heard the rip. It was over my crotch region too. Thankfully I had boxers on but was still pretty embarrassed.

Thankfully my boss was cool about it and I just drove over to Costco down the street and got a new pair and changed in the back of my car. He make a joke when I got back which was fine.