For me a nice mix of vintage and new. I'm size 40 so vintage is doable. With vintage jackets there is usually less money on the line and for longer jackets, at least in my limited experience, the drape is often better on vintage. I also like the feeling that the jacket and I are both coming together with lots of unshared history behind us - I enjoy a jacket that isn't entirely about my own story. But -- I also love new leather and enjoy breaking in a brand new jacket from scratch. Denim has to be raw.
I've got a mix of both. I DO love the aroma of a brand new leather jacket but hate the price. When buying used, I look for as new as possible, the A2 I just bought was 1/2 the price of new and honestly, they guy might have worn it a few times.
The nice thing about a new jacket, espeicially after you've had it for awhile, is that it's entirely yours: every crease, nick, and scrape was made by you. If you nailed the fit when you bought it and it's exactly the style you wanted, it's worth every penny. Also, when I think of some of my old leather-jacket-wearing friends' personal habits, well...
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