Interesting topic. Okay, so I have a bad habit of getting a pair of shoes that I really like and wearing them all the time. Until they die. The worst were a pair of these light tan cloth boots I got from Wal-Mart that had lime green shoelaces and clear bottoms.
I think I had them around fifth grade and wore them way past their expiration date. They were covered in black scuffs by the time I stopped wearing them. I think I ended up breaking the shoelaces and couldn't find others long enough.
At the moment, my favorite shoes are these brown slides with black thread stitching on the top in the shape of vines. They're quite nice. I've gotten plenty of compliments on them, even from guys, which was really surprising. But they're kind of dying. The rubber on the heels is pretty much all gone, so I'm sure they look funny now, but they're the most comfortable shoes I have, and when I have to walk a mile on campus, I want my comfy shoes.
Also, I admit to wearing jelly shoes. But I was young and had no say in the purchase of my shoes. I hope. And I think there was a year or two that I also might have done the different colored shoes. So there, I confessed it all.