The most I've spent on any bag ever was an old school navy MJ Blake on eBay. It was barely used and $450, and easily my favorite bag...oh the turquoise suede inside! I did get 30% cash back from Bing though when they had that crazy eBay promotion. Now, my comfort zone is ~$200-$250. Just got a mini Kristin satchel in turquoise with my PCE, and that came to $250-ish. It was up there for me, but I just had to have it!