Mine is an acrylic sweater with a black and white abstract pattern that I’ve had since I started high school…which would make it approximately twenty-two years old. I wore it when I went out the other night, and I think it’s still looking pretty good!
What clothing have you hung on to through the years, and do you still wear it?
An LL Bean field coat that I’ve had since high school, which isn’t as far back for me, but I’d say it’s close to ten years old now.
That I still wear regularly? A dark green zip-up hooded sweatshirt. It dates back to grad school, so I got it sometime between 1978 and 1983.
I don’t know if this counts but I have a couple of vintage suits from the '60s, vintage shoes from the '40s, and a couple of vintage purses from the '20s and '30s that I still use.
They all belonged to family members of mine (great grandmothers, grandmothers, mother), but I didn’t buy them and keep them.
I have at least two sweaters and maybe a necktie or two that I’ve had since I was in college around '77-78. I’ve also got a pair of dress slacks from the same time which are now about an inch too small to wear but I’ve never had them altered.
I just can’t figure out how they shrank. 
My oldest garment isn’t one that I wear anymore, but I could - it fits me. It’s my blue prom dress from fall 1968 when I was Homecoming Queen. Can’t find the tiara from that memorable night, though. Must’ve lost it in the backseat of the Homecoming King’s car.
I still wear couple of WOMAD t-shirts I have from the 93 tour.
Probably a gray sweatshirt I have. It wasn’t originally mine. It belonged to a friend of mine and she left it at my house and eventually told me to just keep it. But it wasn’t really hers either. It originally belonged to another friend of ours. So I have no idea how old it really is. I still wear it to bed at least once a week in the winter.
Mine technically belongs to the Partner Slip, but I’m the one that wears it.
It’s a tweed 4/5 length coat from the 1940s; he bought it at a flea market in London. It’s the perfect weight for cool days (30’s to 40’s).
I’ve spent multiple times as much on reweaving as the coat costs new, no doubt.
I’ve an old concert t-shirt from the last tour 10,00 Maniacs did (with Ms. Merchant) from 1994 or so. I still wear it on occassion but I’m more hesistant these days since each trip through Laundryville bangs it up a bit more.
I have an even older “Don’t Panic!” t-shirt dating back to c.1990 which I still wear but the concert shirt is more irreplacable.
Congratulations! (about the dress size, not the Homecoming King) 
My Celebrate The Bicentennial underpants from 1976.
I have a shirt that my grandmother made me in oh, 1979. It’s been hanging in the closet of every place I’ve lived since then without having been worn. I haven’t worn it because it’s a hideous shade of turquoise and made of a stiff kind of material. I can’t bring myself to throw it out, because there is only one, and it was made by my grandma.
I guess next oldest is the shirt from the suit from 1980 that I used to own, which got lost in a move. I was all out of clean shirts one day last year, so I got it out and put it on, and couldn’t do up the buttons. I haven’t weighed 150 for a long time…and 170 is a tad too large to fit that shirt anymore.
I have underwear from the 80s. DeHusband actually still wears a pair of briefs that his mom wrote his name in before he went to Boys State in high school. They are insanely threadbare but it’s his only grasp on being a 32 inch waist and he’s not letting them go. (They’re at least 35 years old.)
Cite?
Why, thank you kindly, DB. I can’t take the credit for being able to wear it, though - that belongs to the genius surgeon who performed the gastric bypass that allowed me to lose a whole lotta poundage. At one point, I was a size 26; now I’m a 10. Still losing, too - I expect to be an 8 by next spring. Life is good.
Alas, the Homecoming King is dead. Died in his 40s of bone cancer. Poor guy.
I have two:
A 20th anniversary sweatshirt from Walt Disney World (which anniversary was 1987, so it’s 19 years old).
My camel-colored leather jacket, which I got as a high school graduation present in 1985 (21 years old).
I still have some of my old clothes in the basement, mostly beacuse I haven’t thrown them out yet and they are a little too ratty for goodwill donation, but the oldest thing I own that I still use every day is my white and blue baseball cap.
I bought it when I was in 7th grade at American Eagle. I don’t like a lot of their stuff, but I was walking through the mall and saw this white hat with a blue star and thought it was great. I am now a Junior in college and wear it every single day (or at least 4 days a week). It has been through a lot, being run over by a motorcycle, being chewed up by a dog, and even being lost for a week! I know it needs to be thrown away, but I can’t bring myself to do it and I can’t find a hat great enough to replace it.
Brendon
A t-shirt from my first big rock concert, The Rolling Stones in 1981. I haven’t worn it in over a decade but it will still fit.
Oldest in terms of age is the 1890’s bodice I have. Oldest in terms of me being able to actually wear it- I have a sweater from grade nine, which would be… 1992. Fourteen years. I’m rough on clothes, and most things don’t last too long.