I bought the Gabrielle bag (large size) to use as a travel day bag, against all of my friends' advice (they all think it's ugly). I was shocked at how easily scuffed that base became after a week of sightseeing, and I hadn't been particularly hard on the bag (never put on the flooror under my seat or dropped or anything!).
I have no regrets buying it, but it's definitely a polarizing bag. My friends will unabashedly tell me "Bring a nice bag for dinner. NOT Gabby."

I don't see it being as classic as a Boy, or maybe even a 19. But if you like it and it makes you happy, then buy it! (At least the small size, while impractical from a storage standpoint, is also less bulky, so you can enjoy the lovely two-tone hardware without the heft of the chunky base, etc.).