The Obvious - I truley believe only the stupidest and most attention desprate person on the planet would add extensions to only the sides of their head. I felt like grabbing one in each hand and shaking them while yelling out "On Dancer on Prancer..."
The less obvious but perhaps even more annoying - The Strap Perfect. I have one of these things, they are very useful in keeping bra straps underwraps when you wear a racerback shirt so you can avoid going out in public looking like a total skank. This skank decided to use hers under a regular tank-top so that we could all get a clear view of her bright blue bra straps.
*You can only "win" against someone when you're judging them based on things they have control over. Their hair, their clothes, their makeup, the way they are acting, or some other embarrassing self-"controled" quality the may be exhibiting are all worthy of a "win".
Mental and physical disabilities don't count. Mere ugliness doesn't count. Morbid obesity does count, though it might not be featured on the site unless that person also has some other losing qualities going on (a mullet or a face tattoo, for example).