I have four low-four-figure designer bags, all of which were bought on vacation. I found a Chanel evening bag in a consignment store on a trip to New York with, coincidentally, a passel of YLF friends in tow. Authenticating it and buying it was one of the highlights of the trip!
I bought a Burberry bag at the flagship Burberry store in London a few years ago and again, it was a fun experience as well as a great bag (which I still love and use).
And on my most recent trip to Paris I visited the Louis Vuitton store and a friend and I bought the-same-but-different-color crossbody bags. Again, big fun featuring doting salespeople and champagne.
Oh, and a few years ago a Pride-striped Etienne Ainger bag jumped out of a store window in Munich and followed me home.
These days it's usually cheaper to buy expensive bags in Europe due to the exchange rate and the VAT refund.
They are all beautiful quality and I would say a step above, say, Kate Spade. But really I treasure them largely for the memories they represent.