My first designer bag was Gucci. I purchased it with my first bonus check. It's been an ongoing tradition every since then. Every year I purchase a designer bag with my bonus check.
The first designer bag I got was a vintage Mulberry congo bag from my grandmother, but the first one I bought myself was a Chanel backpack from a thriftshop.
I must be the least sentimental person here ... I don't remember my first designer bag. My guess is that it was Coach, it might even have been a used Coach bag from e-bay but I honestly don't remember.
I started with Kate spade in college then fell in love with nylon prada then the traditional fendis then tiny leather Gucci w horse bite then a dior driving bag. I use them all stuff except Kate spade and nylon prada.
My first "real" designer purse was a Coach "court" bag in black, that was back in 1994-95. Unfortunately, it was stolen and never returned. I've had a ton of other Coach bags since then. My first luxury handbag was the Louis Vuitton Artsy
I'll go all the way back to the mid 80's with a Liz Claiborne, which, I would say was probably comperable to what Michael Kors is today. I remember buying it at Gimbel's (they went out of business in the late 80's). After that it was t Coach and D&B in the 90's, and Gucci in the 00's.