Generally I don’t have a hard time getting rid of things. I used to, but living in small apartments and moving frequently somehow cured me of my previous problem of clinging to everything from ticket stubs, socks with holes, and magazine that I’d read three times. However, one of my biggest hurdles is still getting rid of clothes.
What makes it even harder is that practically all advice I see on sorting and purging wardrobes sounds something like this:

I think we have a problem...
- try everything on
- make piles of keep, toss/donate and fix
- fix the “fix” pile, toss the “toss” pile