This is a great question. I often store things and then later, inspired by this forum for example - I'll think 'I sure wish I had kept that' only to go 'discover' it in storage and then bring it back into rotation. For me, the secret is I need to be more selective on what I welcome into my closet because I have the hardest time editing things out. I get rid of things if they are in horrible condition (sweater pilled beyond repair), really uncomfortable or truly do not fit but aside from that I am often too scared I'll later regret it.
Just like now - i'm wishing I'd kept those denim shirts from the mid- 90's!
So I suppose I'm not much help but I appreciate you bringing up the question.
Oh, and I will say I have been enjoying some success with consigning and ebay this year so when I do get rid of stuff and get money for it it feels good too b/c that way I can justify buying something I will use more. So sometimes that does work for me!