I probably went through about 20 different outfits for this particular round, and I had the hardest time landing on a race. By the time I finally decided what I was going to submit I ended up with a brief description of the character looking something like this:
"I figured goblin suited you because they seem a little shifty to me (something shifty only seemed to fit given the evil nature of this round). So anyway I figured being pretty much the king of transmog contests that your npc should be dressed good, so I totally pimped him out. This goblin is stylin’ and ready to judge some outfits! Oh, and to add a little bit of badassness to the look (cause we all know your a little badass) I threw in some brass knuckles so nobody would mess with ya!"
Items used in this Transmog & Source:
Stylin' Adventure Hat - Leatherworking (350)
Mantle of the Desert's Fury - Princess Yauj, AQ40
Black Dragonscale Breastplate - Leatherworking (290)
Sentry's Gloves - level 25 - 30 world drop
Impenetrable Bindings - level 50 - 55 world drop
Vindicator's Chain Girdle - vendor Kayri, Isle of Quel'Danas
Bloodmail Legguards - used to drop in Scholomance (unfortunately no longer available in game)
Pillager's Boots - level 30 - 35 world drop
Stylish Black Shirt - sold by Lisbeth Schneider, Stormwind City
Heavy Iron Knuckles - Jewelcrafting (125)
See this transmog on other race models: Wowhead item comparison of this set
Check out how the other entrants portrayed JD and the results of round 3 here: The Amazing Transmog Survivor Contest Round 3 - Build an Amateur.