... Otherwise I have this terrible tendency not to wear an item because I love it so much I don't want it to wear out.... yes I really am that crazy. ...
Be assured you're not alone in your 'craziness'. I do the same thing. I sometimes buy something I love soooo much that I'm afraid to wear it because I might get a stain on it, or damage it in some other way, or yes -- wear it out. Some of my most favorite clothes are my least seldom worn!
I do the same.
I love people who are well dressed ad well put together. I, however, tend to look pretty shabby and just grab the same jeans and tshirt out of the closet. So I decided to do a huge purge in my closet, create a kind of capsule wardrobe, where everything looks good with everything else, and only leave only things I wear and love.
This morning, I was getting dressed to do some errands (bank, grocery, that kind of thing). I reach into my beautifully organized closet and pull out a nice grey pair of pants, a burgundy knitted top and matching burgundy flats. Nice, chic and easy to wear, right? So, I put them back in, thinking they are too nice to wear. Yes, that does defeat the purpose. (note - I wore the nice outfit)