Thinking about a dresser full of clothing, some of which is fairly elderly, I got to thinking about the oldest thing I have that I still wear regularly.
It’s down to a T-shirt, that I bought after seeing The Secret Garden on Broadway - late 1991 or perhaps early 1992, or a paisley silk shirt-dress bought at about that same time - hopelessly outdated style, but the fabric is so wonderful (the underlying weave has a paisley pattern as well that you can only see in certain light and certain angles). but I haven’t worn it in years. I still might though, so I’m keeping it. The T-shirt would have to win, though, since I do wear it regularly. Its days are numbered, since there’s a hole in the fabric at one spot
Let’s rule out heirloom-type things - like Grandma’s fur coat; keep it to regular things - bought specifically for you, but I guess a hand-me-down of a regular garment would count. If I counted heirloom stuff: I have a mink headband! My mother had her mink jacket, inherited from HER mother, cut down as parts of it were getting pretty ratty. That would put the thing at 70+ years old.
I rarely wear it any more but I have a green Navy utility jacket that wasn’t new when I got it in 1986. Problem is it barely fits now. But it is warm and I use it for some extra dirty jobs, like chain sawing downed trees. I think this jacket is from the 70s, so less than 50 years old.
How often does ‘regularly’ have to be? Does once a year count? If so, I have ‘special’ Christmas socks my grandmother made for me in 1963 or so. Only worn for a couple of hours on Christmas morning.
I have a Levi’s jean jacket from the early 1970s. It’s a style that Levi’s apparently stopped making decades ago (it has a horse blanket lining). My dad was given it as a gift around 1972, but it was too small for him; he hung onto it, thinking that I would grow into it when I got older. I started wearing it around 1979, and wore it all through high school and college – I never got as tall as my dad, so I never grew out of the jacket.
It’s kind of beat up now: the edges of the cuffs are frayed, and one or two seams are starting to come apart. I still love the thing, and I still wear it a few times a year.
I have a jacket from 2001 (when I was a sophomore in high school) that I still wear regularly during the wintertime. It was a Christmas gift from my mom. It has special pockets for a discman and a flip phone.
My sister gave me a black fleece anorak in 1995. It somehow refuses to get lost or damaged like the rest of my clothing.
I have a rash guard that I bought on honeymoon in Hawaii in 2001. It’s about ten sizes too small now, but I can’t throw it away because it was super overpriced and I keep thinking I’ll lose enough weight to get back into it. I have a few items of athletic clothing like that.
Funnily enough, lockdown is killing off my old clothing collection as I’m wearing them a lot more due to not wearing office clothes. In the last few months I’ve finally thrown away a t-shirt dating from about 1983 and a pair of trousers from about 1989 as they finally wore out beyond use or repair.
I still have an assortment of t-shirts from the late 1980s though. Still wear them, and they still fit.
I have two acrylic sweaters that I got for my first year of high school, 1984. I’m 51 now and have worn them every winter between now and then. They’re pretty cool-looking, I think. Eighties geometric designs.
My Burberry trench coat. Bought it in the Burberry store at Piccadilly Circus in 1991 or 92; the real thing, custom fitted, with my initials embroidered in the lining.
It was a very British experience complete with a snotty Junior sales clerk straight out of “Are You Being Served?” eyeing my comfortable traveling clothes and commenting “Get a bit greasy that way, eh?” The Senior with the tape measure around his neck glared at him over his glasses as I handed over my wad of US $100 bills.
My favorite T-shirt is just a basic dark-blue shirt with a white “33” printed on the front. I definitely remember that I already had it when I was 33 years old because I used to joke that that’s my age when people asked me what the “33” meant. I still give that explanation, though I’m turning 54 in a few weeks.
But that’s not the oldest, right now I’m wearing a synthetic fiber jacket I used to wear when horse-riding, and I gave up riding more than 25 years ago. Now I wear that jacket only inside the house in the winter for comfort.
The oldest may be the only suit jacket I own. My father gave it to me about twenty years ago when I needed one for a wedding or a funeral. He had owned it quite some time before he gained too much weight to fit anymore, so this jacket may be 40 years old.
Do shoes count? Back in 1984, Sperry Topsiders were all the rage. I bought a pair. Throughout the decades, they’re my gardening and walk-outside-for-a-minute shoes. They stay by the couch, so I can slip them on, take out the garbage, go out to the garage, whatever. I’ve replaced the leather laces twice, but the things are going on 40 years old, and still wearable.
I have a tuxedo from c1994 which I still wear when I can fit into it (at the moment I can, my weight fluctuates quite a bit, mid 2021 I could not) and have a need to. But since the pandemic I have not needed to.
I also have a ski jacket and ski bib from around that same time that I do wear regularly. It’s a bit snug but not uncomfortably so. Worn when I am clearing snow with my snow blower or hiking in the woods. I also have very comfy snow boots from that same purchase that are still serviceable but not really presentable.
I have a couple of jackets from tracksuits that date back to the early 1980s. They’re not the height of fashion, but they are comfortable and warm. Fashionistas may sneer at polyester, but it lasts.
The t-shirt I bought at Prudhoe Bay, Alaska. It has a map of Alaska on the front that shows the route of the oil pipeline. I bought it when we drove up there in about 2006 or so. I like it because it’s comfy and I’ve never seen anybody else wearing one.
A sweatshirt I stole from my boyfriend in probably 1999 or so. I’ve had it longer than I’ve been on the SDMB! I wear it almost every day in the winter, as I’ve always worked from home and it’s comfortable. Not too tight, not too loose, not to warm, not worn out.
We’ve been broken up about 20 years now and he was a POS but the sweatshirt is still in fine condition.
I normally don’t recall specifically what year I acquired various clothing items. The exception to the rule is when that item has a year or an event printed on it. I have a tee shirt I wear frequently that advertises National Eye Exam Month for Sears in 1995.
I have a Gloria Vanderbilt gift-with-purchase purple umbrella with a white plastic swan’s head (the swan was part of Vanderbilt’s clothing line logo) handle made to look like marble. I’ve had it since the 70s.
Once I left it at my seat at a hockey game at the Fabulous Forum. I thought it was lost for good, but walking to our car I saw a guy walking with my umbrella! I walked over and recognized him from being in our row, which confirmed it was mine, plus, well, how many guys have purple swan’s head umbrellas? He was happy to return it to me, and I still have it and use it.
