Kairi, Kingdom Hearts II
The Look: All grownup, clown feet
The Crime: Impractical

To be fair, Kairi didn't know she was going to have to be running around in that, uh, "dress" when she gets nabbed by Organization XIII. But still, why in the world would you wear a dress with three zippers up the front and none up the back? She's only got A-cups (B max), so nothing is going to fall out as evidenced by the fluffy white training bra she's proudly sporting underneath. The black hood on the back of the dress wouldn't even cover half her head, and when paired with the belt contraption, the whole outfit says: "I haven't come to terms with puberty and I get dressed in the dark."