Part of my journey to becoming more minimalist to to get used to letting material possessions go. I remember a specific moment that my current favorite shirt got a hole in it due to splashing a little bleach on it. I really did like the shirt a lot. But for the first time in my recent memory I convinced myself it was nothing more than a piece of fabric and I shouldn't wrap emotions up in it. I accepted the fact that the shirt was ruined and moved on. I actually ended up cutting that shirt up into a headband that I will wear to this day.
Whenever we go through our closets or drawers to purge things we don't want or use there is always that part of us that has a hard time letting go of things. What if I want to wear this again? What if I need it later? Even though you haven't worn that or needed that in six months we still have a hard time getting rid of it.
I'm much better at this than I used to be and I plan on getting better and better. I try to see things just like I saw that shirt with the hole in it. Just an item that shouldn't have emotions attached to it. Our emotions should be wrapped up in the experiences we have, the things we love to do, the people we love to do them with.