That’s a tough one.
Either an overcoat that my grandfather gave me, his father had it before him. It’s a vicuna fur coat, very rare, and about 100 years old. Not many opportunities to wear it but it’s got such good history.
My leather jacket, first really expensive designer piece I bought entirely on my own. I bought it 2 years ago and still wear it day in day out come fall/winter/spring. Just nice to know that I paid for every cent of it in full, even if it was heavily discounted.