I used to do the same with my computer files. I used to be one of these people who are crazy about back up. Then I realise that it is not important to back up everything. There are some things that need back up. But there are things that are not that important. So really, why bother.
I used to get irrationally attached to all my clothes/shoes/bags. This is perhaps the silliest attachment of all, given that I didn't wear a lot of them for various reasons. So I let go of all of the ones that I don't wear and/or don't love any more. It was very liberating and I do that on a regular basis now.
The only thing I don't really get attached to are people. Since a very early age, I accepted that people come and go and none of them really stay in my life for a long long time. There are a few who are kind, loving and understanding and are always around when I need them most, but that's about it, really. Most people come back and forth, drift from one spot to another. Sometimes our paths cross and we got together. I have very few people that I miss constantly. I miss various people in little bits and pieces every now and then.
The same thing happens with places that I have stayed in. I have moved so often in my life that I don't care where I live any more insofar it is nice and comfortable. I don't miss particular apartments that much. I don't miss places that much. I just focus on enjoying where I happen to live at the moment.
I think a lot of what we are attached to are not necessarily things that we place a lot of value and importance to. It might just be by accident. Or maybe, laziness. Letting go is a lot easier once we have made the decision to do so. In fact, I cannot imagine my life any other way these days.
Have a great weekend!