Please put me on the bench!
I bat for Team Pristine in the sense that I like my things to feel new and fresh and to look crisp (if that is their nature) and immaculate.
Also, when I buy a new item, I almost always "crush" on it --- I want to wear it all the time (and sometimes I do!) Unlike your friend, when I love a piece of clothing, I want to work it into my outfits in as many ways as possible. No "two wears and you're gone" for me. It's more like: OH. YOU are my new favourite jeans so I am going to wear you all week! Maybe I'll wear you all month!
In fact, I'll bet if I tracked my wear patterns more minutely, I would discover that I get by far the most wear from my clothes when they are new, and certainly within their first season. I keep most things much longer than one season and continue to wear them, but they have to be really special to earn the same kind of love from me as they did in their first season in my closet.
But, I'm on Team Broken In in the sense that certain items -- especially footwear, jeans, and some jackets -- really seem to come into their own with continued use and I appreciate this quality and enjoy it.
Oh, and also Team Broken In because I love Claudia's dog pic!