1. Someone who thinks they did something cool and then acts like they're the shit.
2. Someone who thinks they're just plain cool.
1. Guy1: *Scores high in Dragon Punch* (The game commonly seen at bars, where you punch the fuckin thing to see how strong you are.) *........Walks away.*
Guy2: "...What a cooley wooley..."
2. Guy1: *Wearing a cowboy hat or something faggish at a club*
Guy2: "...Hey, check out that cooley wooley."