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Interesting questions and comments. I'm on team broken in for sure...well, even team beat up, honestly. I love patina and texture in denim and leather and waxed jackets for example. Many things to me look and feel better with age. But I also really love the juxtaposition of something very broken in/beat up...jeans or boots...with something crisp and pristine looking like a tailored shirt or jacket...as long as the feel is not restrictive.
Aquamarine nailed it for me. Pristine when headed out of the house. Broken in when at home. I like to save the newer pieces for outings in hopes that they will stay looking there best longer.