A winner is a person and/or persons that dress, look, act or are otherwise extremely trashy.
These people generally have mullets, poorly died hair or other distasteful hair cuts.
Their dress code is generally short shorts, fluorecent colours, clothes that bare more skin than the person should show and can often be found smoking.
"Hey Ziyi look over there, she's a big winner"
"There's no denying that she's a winner look at her hair cut it just screams winner"