eS Evant (The Koston 3 Reissue) I didn't get the Koston 3's as a kid, so I was interested in this reissue, even though it had a totally different outsole (and obviously, no airbags in the heel). One of our local rippers had a pair and when he said the outsole was "okay", that was my cue to buy a pair at half price when they moved to the end of season clearance sale.
Disaster purchase. The outsole sucked right out of the box, and what little grip it did have, eroded quickly. Then one of the lowest hidden lace loops BROKE on the outer-facing side of my left shoe (I'm a regular), and since there were no other lacing options, I had to start lacing them from the second lowest set of loops, which made that shoe fit all weird. I was really glad I didn't pay full price for those. They were comfortable though, and got plenty of compliments, but could not handle skateboarding, or at least my shitty version of what I call skateboarding.
Also, the Vans Rowley Rapidweld. I was truly disappointed at how quickly those fell apart, especially considering how Geoff Rowley has always been one of the toughest skaters out there. I fell for the waffle's marketing there.