By oldest, I mean closest to beta/launch. My oldest item which I am still in possession of would have to be The Supremacy from the original Queen's Wrath event. I also have 2 Jackolytes and 3 Flight of Shadows.
EDIT: My other vanilla items are Deviant Gravity-A, Perun's Fire w/ Accelerated Coils, AOS#Cryptid gauntlets, Ghost Angel boots, Ghost Angel cloak, Dustwalker cloak and the vanilla titan IB class item.
EDIT 2: I forgot about my vanilla Dead Orbit and New Monarchy titan marks.
EDIT 3: Uploaded picture of my very first ever legendary gear drop : )
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The Vanquisher 8 vendor version pre dark below.
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Chasing infinity , titan queens wrath helm . there may be more but I'm not sure
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Beta emblem, hunters first queens wrath helmet, vanquisher and shadow price.
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Thorn day one
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The white weapon you get at the start of the game. and my ghost angel cloak. love the look of that cloak