I just bought my first "high end" designer bag that is also the most I have ever spent...a Prada Cervo Lux Lace Print Bowler. $1500 used. Havent gotten it yet but am eagerly waiting its arrival!!
My croc birkin with diamonds. Sadly, I hardly ever use it because I'm usually in jeans and a t-shirt or jeans and a hoodie, and that's just not the bag for that kind of outfit. Lol.
I spent $3500+ on a Chanel caviar flap. I couldn't believe it at the time that I'd actually gone and spent that much for a handbag. I put myself on purse ban for a long time after that.