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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So much old stuff - The Titan Helmet, Chest Plate and Mark from the very first Queen's Bounty event (the helmet looks like it has a crown). Also Jolder's Iron Sash from the very first Iron Banner. When I started my first Hunter I kept his starting Cloak (scarf) because it lets you see the full helmet (360 degrees), and kept his Khostov for sentimental reasons - that cracked sight gives me feels. Have a number of vanilla armor pieces that I just like the look of (mostly for Titan, like Arihant and Toutatis, but also a number of Tengu Operant pieces for Warlock). I had saved the Handcannon NIFTY_BISCUIT since I first found it (pre Crota's End) - only JUST deleted it as I finally found a higher attack version of it - I just loved the thought of using it in Crucible and having someone's screen tell them they were killed by The Nifty Biscuit (never was very good at killing people with it, but, whatever). Never discarded any of my copies of the Stranger's Rifle - was delighted to see them auto-convert to legendary. Have almost the full set of Vanilla Legendary Crucible Armor for Titan (DRGA-GNT, missing chest I think) because I liked the flavor text - saved a rare Pulse rifle called Echo-33 and several random other items with Exo themed fluff for the same reason. Kept the special Gauntlets you got from Eris Morn for doing the multi part Urn quest (which seems to be gone now?) for both my Titan and Warlock - not sure if I still have them for Hunter or if I never got them... :( If anyone has read this far - do you know if that quest line for Eris still exists and how to activate it? I started a brand new Hunter to try out the Story from the beginning with NewGhost, and have finished Eris's Questline with no luck. I am a pack rat, and would have kept more if I could (though I probably shouldn't). I need to convince myself that there are online databases where I can go read the flavor text (the main reason I save things), and that no matter how cool it looks, I am probably never going to wear it again anyway. God I love this game.