Updated answer: Chanel jumbo classic flap in lambskin - the damage was about $2800.00 - haven't really enjoyed it yet, using my Marni balloon which I am more in love with.
Chloe python Silverado doctor bag...at full price. After that one WENT ON FREAKING SALE after I bought it, I vowed to never again buy a bag that was not either (a) Louis Vuitton (which never goes on sale) or (b) at deep discount.
Ok.... I have been reading all the postings and my MOST expensive purchase to date is mt Chanel Cambon (pocket bag) $3150.... and it's soooo true... once you break the $1000 mark its very easy to do it again.....
I think I have 4 bags over $1,000, and are my most expensive.
Bottega Veneta large Veneta in nero and ebano Both over $1500
LV SO Damier Cabas Mezzo
LV Monogram Multipli-Cite Both about $1300 I think. All of these (not Mulitpli) were "special occasion" gifts, 40th, Christmas, etc.
The rest are under that, and a lot of them were on sale.