What do you think is the rarest/most elusive transmog item in game? Is there an item that comes to mind that would shock you if you saw a person wearing it-game? Maybe the Uldaman rares? I’m sure there are tons of old Vanilla items that got deleted in Cata that are very rare now.
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I’d be shocked to see someone using Miner’s Hat of the Deep (Uldaman), even though it does occasionally still drop. It doesn’t count as the rarest, but I want one eventually. 
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Realistically one you could see; Corrupted Ashbringer.
Unrealistically but literally the rarest; That Legendary Amulet from MC that only 1 person has.
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Both corrupt ash og from naxx and Atiesh I think.
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Except you can’t transmog amulets 
I know I’m always jealous whenever I see someone wearing the unique Judgement recolours from the Pre-Wrath Scourge invasions. Absolutely kicking myself still for collecting the cloth set on my caster druid, since the leather was all agility v.v
The Starfire Tiara/Holy Diadem (cloth helm) would get my attention. It has the Wonder Woman tiara graphic and I rarely ever see it on a transmog. The drops are longer available so anyone who happens to have an extra one in their bank after all this time can sell it for a hefty sum.
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Tunnel Pick is an extremely rare pickaxe that you’d never notice unless you’re a pickaxe connoisseur. I’ve seen it on the AH a couple of times for millions of gold, but the supply of them is obviously dwindled.
Shame, cuz it really blows Cold Iron Pick out of the water.
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Something like the elite wands from s9 are probably almost nonexistent. They’re wands, firstly, so limited to three classes who would have bought them. While they were bought because they had slightly higher ilvl, I’d bet nearly everyone trashed theirs after getting the next seasons wand since transmog didn’t even exist for s9, and they were wands which weren’t really transmogged when it went live anyway. They also were only available for that one season, s10 wands had a different appearance and no other wand shares the appearance/color scheme with them.
Factor in that you needed 2200 rating for them too (not bad in s9 with inflation, though) and that it was 10 years ago and many of those players likely quit and it adds up to them being among the rarest items in the game.
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I haven’t seen
other than on some npcs in the Draenor intro quests. It did have to have the original transmog rules bent to allow it, so I’m assuming that someone important had one. (I think it was blue and had no secondary stats or something like that.)
There must not be any mining pick enthusiasts on one of my servers, or they would have snagged the Tunnel Pick I keep listing.
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Yeah, I think the vast majority of people just see tunnel pick and laugh at the price.
They don’t know the pain of us 2H pickaxe wielders.
1H pick wielders get it all, all the pickaxe skins. We 2H miners are forced to pick between Hogger’s Cold Iron Pick with its dry-rotted looking handle and the glorious Tunnel Pick with its bright and vibrant handle.
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Lots of rare items from Classic that are still in the game and tracked as transmog if you happen to have one, but you can only get them from the auction house for insane amounts of gold. I don’t know if they’re “required” anymore, though.