Sara Little, commerce account manager
"Every cool girl at Pilot Butte Middle School in 1995 was wearing Dr. Martens Mary Janes. Naturally, I needed them. Naturally, my mom said no way. Pricey imports from the UK did not belong in my closet, apparently, but I was determined. When a pair of the Payless versions arrived for my birthday, I would not stand for cheap knock-offs (this is my first real memory of brand coveting), so I managed to save up my allowance for a pair and purchased them right as the next big thing in shoes emerged: the Adidas Samba indoor-soccer shoe. I don't think I ever even wore them once! I have no idea what happened to my Docs, but I'm sure they're boxed up in my parents' garage..."

Dr. Martens Mary Janes, $100, available at Dr. Martens.