It would have to be the Louis Vuitton Suhali Lockit PM.
I bought it many years ago thinking it would compensate for the bag I really wanted (Birkin) and when it came time to selling it, I lost roughly $2,400, which was a tough pill to swallow. I debated on whether I should sell it or not based on resale value, but I wanted the small Chanel Boy more and thought the $800 would be handy in contributing towards the Boy.
I also found the bag dated quite quickly based on its yellow contrast stitching. At that time, I also went through a long phase of loving handheld bags.
Since that happened, I have been very strict in deciding which bags I allow into my collection. That's why I prefer to play it safe nowadays.
Yes, I went through a phase which I purchased a bag, thinking it’s gonna replace something I really wanted. It never worked!
Before I had my career, I bought quite a few bags from contemporary designers - Marc Jacobs, Kate Spade, MK etc. I sold all of them. Now, I am very careful with my bag purchases.
$2400 loss is rough !! I believe many of us made “handbag mistakes”. Same, I play it very safe nowadays! I lost $400 on the Strathberry Midi Lana bucket bag when I sold it.