I still wear my dad’s old USAF fatigue jacket (from back before they were BDU’s) - the manufacturer’s stamp says it was made in 1953.
I have a black US Navy trenchcoat that dates from some time in the mid-70s - still looks sharp, although the belt is missing now.
I’ve got a pair of black leather gloves I bought around 1988 that I still wear every winter - AF issue “gloves, leather, black” that are nice and warm and fit like…well, better than any gloves I’ve ever worn. I can write while wearing them.
Other than that, I’m too hard on clothes for them to last very long. I have a shirt that has faded to a greenish-grey color (used to be sage green) that’s probably 10 years old, and a couple of other shirts that are 8 years old.
I still have a pair of shorts I wear from '77 when I was 3. Very tight. And my voice is pretty shrill these days.
Hm. Seriously, I have a few shirts from '90 or so that I wear regularly. Probably some underwear and socks from farther back. I like to think I rotate out anything that old, but my housekeeping skills are occasionally questionable when it comes to things like that…
I have an old pair of Greb “Kodiak” work boots from high-school, they must be going on 20 years old now. I wear them around the house for yard work, they feel like slippers.
I also have a Minnesota Vikings T-shirt from 1990 which is about 3 washes away from disintegrating. My wife bought me a new one 2 years ago, but it doesn’t have the same feel…
I have a dark green pullover sweater that my dad got when he went to college in the fall of 1966. I wear it a lot in the winter. I also occasionally wear a green military-style jacket that I guess he probably got when he was in the Air Force.
My sainted Grand-Dad’s big lumberjack shirt which I inherited. Its plaid stripes are red, yellow, orange, red-orange, and white. Dates back to mid-century, I guess, but the colors are still bright as daylight.