I just purchased my third. Love the Boy!!
I do have multiple classic flaps, but I would say the Boy bag is easier to get in and out of, to style, and all around more comfortable (you can wear it three ways). I have the new medium, old medium (just purchased), and the small. All Boy's are fabric lined except for exotics. Let me know if I can answer any questions..happy to help
New medium: Caramel/beige lambskin and shiny silver hardware
Old medium: Black calfskin and ruthenium hardware
Small: Dark grey calfskin and aged gold hardware
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I absolutely LOVE this forum and this thread! 
Nowhere else do I feel comfortable obsessing over this particular bag. 
I used to have the new medium boy (in black lambskin) maybe 7 years ago but sold it because I was just babying it too much (and it was slightly too big for every day use). I also sold my boy woc (also in black lambskin) for the same reason.. and also my caviar GHW and SHW (because I really wanted lambskin but felt caviar would be more durable... but I just didn't FEEL for the caviar as much). I felt bad having spent that much money on things I weren't even using.
and the story and design of the boy bags, so my husband finally nudged me into buying a pre-loved old medium boy (in black lambskin w/ruthenium hardware) from 
Even as my husband was egging me on, I was honestly trying to find reasons why I shouldn't do it (I may get robbed while walking around, lambskin is just too delicate for every day use, scuffs easily, chain in heavy, things might fall off, etc.)... but I decided.. you know what, who cares if it scuffs? How badass would it be if I used this bag SO MUCH so that it was scratched, scuffed, squished, etc? THAT is how I can get the MOST bang for my buck. It's not like I'm trying to pass it down to anyone. 
