I have doctor’s scrub type of shirt that I’ve owned since at least my first year of college (1980) and I still wear it occasionally. It seems to have held up pretty well. And I still have some sweatshirts I bought in college or shortly after, including one from 1988 when the Kansas Jayhawks won the NCAA basketball championship.
I have a few great pieces from back when my mom dressed like a hippie-the best one is a paisley cotton wrap skirt.
The oldest shirt I own is some hideous thing I’ve had since I was 6. It went down close to my knees back then. But it’s sooo soft…I sleep in it and anyway the horrible eighties scribble pattern has almost completely faded.
My favourite tshirt from when I was young disappeared a few years ago 
. Back when my dad was in research he went to some conference and brought me back a mint green shirt that said “Nothing Phases a Ceramic Engineer” on the front and some sort of engineering diagram on the back. I loved that tshirt-got it when I was 8 and wore it into my 20s.
My parents wore great clothes back when they dressed like hippies but aside from a few pieces I’ve salvaged my sister and I wore them through during highschool (my highschool was all over alternative/vintage chic). My favourite shirt that my sister and I used to share fell apart in the washing machine and we wore the threads off all my dad’s bell-bottomed corduroys (when he asked my mom’s family if she could marry him she petulantly conditioned the acceptance on him getting rid of the pegged pants and wearing bell-bottoms).
I’m going to India this January and I’m having a bunch of 50s style dresses tailored out of vintage dress patterns in sari material. It’s going to look frickin amazing-I can’t wait.
Most of my clothes are “new” in that I had gastric bypass surgery in November and for about 5 months, I literally dropped 3 sizes a month.
My oldest clothes actually belonged to my mother. Her wedding dress - 1948. The dress she wore when she brought me home from the Childrens’ Home - 1961. Her fox neckpiece - circa 1950s. Her mink stole - ditto.
VCNJ~
The oldest thing I own and still wear is my fleece jacket from 1998 (senior year, track team). Despite gaining 60lbs since then, it still fits.
The oldestn thing I have have and don’t wear is a lovely white dress with a V neck that goes to about 5 inches past my boobs. It’s actually kinda creamy white and has hand painted red flowers on the very flowy skirt. I have no idea how old it is but the person who sold it to me said it was at least 20 years old.
Nuthin’. I’m hard on clothes. I can destroy a pair of jeans in a coupla months. I wear clothes out quickly, and my wife chucks out any old stuff. I doubt I have anything older than about four or five years.
I have a black button down short sleeve shirt that I got at a vintage clothing store in 1984 or so. Lord knows when it was new. I also have almost all of the T-shirts I had through college (same era).
My back-up pair of hiking boots I just recently retired. They were about as old (20 years, +/-). They are still in wearable shape but they don’t fit me so well anymore.
The piece of clothing that’s been with me the longest is an Argyll & Sutherland regimental tie I bought at Brooks Brothers on my first trip to NYC in 1982. However, I have an extensive vintage tie collection, some dating back to the late 1930s.
I used to do the vintage suit thing, but I wore too many out and they got to be impossible to find. New suit styles also got niftier, what with the renaissance of the 3 button front during the 90s. (I remember when only Brooks Brothers-type places had them, and they were cut so you couldn’t button the top button or you looked like somebody’d grabbed you by the lapels and shook you.)
I have a 1908 cream silk satin evening gown. It doesn’t fit- I’ve gained weight since I bought it eight years ago, and I always needed a serious s-bend corset to wear it, but it’s lovely, with asymmetrical bodice draping, silk lace, and frou-frou silk chiffon ruffles on the lining.
I’ve got a late 30’s wine silk velvet dress, and a mid 30’s little red housedress that I wear occasionally. I think it’s rayon.
One of my friends bought me a gorgeous 50’s evening dress, in red/midnight blue shot taffeta. It’s got batwing sleeves, a slit v-neck, and a circle skirt. I love it.
My favourite piece I think I might sell, if I can find a buyer. It’s a midnight blue silk velvet late twenties opera coat. Perfect condition, and beautiful, but it doesn’t fit anymore, and I’m scared to wear it anyway, for fear of damaging it.
My oldest piece of modern clothing is probably a sweater I got twelve years ago.