Oldest article of clothing that was purchased for me: a pair of Umbro soccer shorts my mom bought for me when I was in the fifth grade. (I’m a junior in college now).
Oldest article of clothing I own: My dad’s denim jacket, purchased around 1974.
Well I’ve got an old navy P coat that was a great uncle’s. Probaboly 50 years old or more. I don’t wear it though.
I’ve got some underwear that have to be at LEAST 7-8 years old and are probably older than that. They have been all around the world and I still wear them. They are getting pretty worn though and I have started to buy new stuff.
I have a woolly jumper from my Grandfather that he had when he was a student at Cambridge in the early 1930s.
It’s a really nice thick jumper, very warm. You would never guess it was around 70 years old; it certainly doesn’t look it.
Oldest thing I bought and still wear… a woolly jacket from schooldays, let me see know that’d be c.15 years old.
Oldest article I bought new—a cotton sweatshirt that I bought about 1968, when I was 11. It’s worn to a velvety consistency now, though I only wear it around the house on weekends.
Oldest, period—a silk chiffon dressing gown from about 1926. It’s lavender and red, and has lavishly double-ruffled hems on the sleeves and bottom, using yards and yards of fabric. Just the thing for lounging around reading Snappy Stories and eating bon-bons.
I have a Polo shirt a gilr I was crazy in love with bought for me 13 years ago when I was in gradute school. Even though it was 8 years before I met my wife, I have never mentioned to her where it came from despite the fact that it’s BRIGHT PINK!?
Oldest iteam I still occasionally wear: short sleeve button down shirt - white with pink stars. Yes, it screams “Eighties!” 'cos that’s when it was purchased.
Used to have a Navy pea coat - bought second hand, donno how old.
My prom dress was a vintage 60’s [?] formal dress that I added a cape & ruffles to.
I have a thing for antiques, resale, vintage stores.
I use to own ( not sure where it went) my dad’s old hawaiian shirt that was from the 40’s.
My old (female) boss gave me one of her old dresses that is from the fifties, with a mink collar and mink on the sleeves. Not very PETA, but I just love it.
The oldest thing I wear on a regular basis is my late grandmother’s wedding ring - a simple band of white gold with markings. She married my grandfather in 1920. I also wear my mom’s wedding ring ( doesn’t fit her anymore) which is also a band of white gold) from 1948.
The only thing from my teen angst years that I just recently got rid of, and wore on a regular basis was a single pair of white cotton underpants. They were from 1980. After twenty years of weekly washings (and that monthly time thing) the thing was practically transparent ( except where my mom wrote on the waist band my name for camp.)
I have riding boots that I bought in England about 20 years ago. They’ve been resoled, but they are still going strong.
StG
My winter coat is a brown “bomber” jacket I got for christmas in of 1989 and a pair of cleats (shoes) that I got right after my 16th birthday (also 1989). The jakcet is very ratty and torn and stained, it has character. The cleats are in even worse shape, not much cleat on the right foot (dont put your foot on the ground going ~50mph) and had lube stuck in them by my boss when I was stationed in Florida. It actually keeps the water off of my right foot. My best baseball/softball glove was purchased when I was 13, but thats not really clothing. Until my last move, I had flannels from middle school(mid 80s).
dead0man
An INXS tshirt for their KICK tour of '88.
Sometimes ya kick. Sometimes ya get kicked Maybe you had to be there. 
~t
I have a green army wool coat made in 1939 in Toronto. It has the factory label still attached, but I don’t remember the name of the manufacturer. It’s lined with canvas, and it has the name “Duncan” written on the inside pocket.