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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Day 1 emblem and my zombie apocalypse
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Beta emblem/ day one emblem
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My Titan emblem, true day 1 promotional exclusive.
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My Raku Crucible type helmet from week 2. I love that thing so much.
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The Devil You Know. Still at good ol' pre-TTK 300
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Idk why, but i still have vanilla hunter armor in my vault (ghost angle chest and helmet) and i dont even main a hunter...
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I still have the default armor for my warlock in my inventory. Not sure if they changed it in year two or not though.
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The kholostov.
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White ghost
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My launch day emblems
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Thorn from the first week which was hell to get
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My Universal Remote...first exotic I ever got and it dropped as my first legendary engram from the loot cave.
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I got icebreaker first few days of launch.(2014) Less than a week
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Dustwalker boots. Was helping a friend level up by doing some lvl 20 Vanguard strikes pre-TTK, and started decrypting engrams. You know what happened next.
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Jackolytes and Flight of Shadows. Oldest weapon besides my launch day Khvostov is Three Little Words
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Suros followed by ice breaker.
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Khostov
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my e-receipt to buying day1 digital edition for xb1
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The OP Khovostov
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Deviant gravity a
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Zombie Apocalypse WF47.
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Jackolyte and tumbler
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Zombie spa collapse, got it end of week one,
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All 3 vanilla faction cloaks and all 3 vanilla faction hand cannons
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Still got jackolytes, the original warlock bonds for dead orbit and new monarchy and a couple vanilla heavies
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Aries Nemesis I got on day 2