Probably 5 times, give or take.
For me, it wasn't clothes, though, it was just my collection of transgender fiction that I wrote. I've deleted them, told them I was never going to write transgender fiction again, and then subsequently re-written the exact same story all over again, at least 4 times.
I also did one big purge where I threw out my collection of ACE bandage and fish-tank tubing that I used for genital tucking with sit-down urination, plus threw out my water-balloon-boob collection along with it. (I used to stick water balloons in my shirt and leave them in all day to simulate having boobs, and even slept in them several times.)