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A 100% cashmere overcoat - black - that is 15 years old which I love.

A navy blazer (cashmere) I bought for my mother in Scotland 17 years ago, and which I now wear.

A charcoal grey fine wool bespoke pants suit I had made to measure by a master tailor who trained in Saville Row, which he made for me ten years ago.

A few (tailor made cashmere & wool) jackets, made to measure six years ago.

There are more; I buy very good stuff which I expect will last me for years.

Several pairs of Church's shoes (made to measure) from six-seven-eight-to 10 years old.
 
Plain blue 3/4 length wool coat for 0* days approximately 1948 vintage.

Or 1990 sub-zero LLBean wardens parka 3-layer down filled for -35* days.

Last would be waterproof, wind proof, 1960 Austrian wool pants and Sorel’s with felt liners for extreme cold.
Comfy to -60*, hate long underwear.
 
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Another LL Bean item: I have a fleece hooded anorak from 1994 (which they stopped making) and I still wear it regularly. It is a very treasured and loved item.
 
Various shirts that were purchased 1980-1988.
The one that gets the most wear is a super-soft plain polo shirt from Mervyns, the texture of which hasn't been matched since.
 
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Patagonia 1/4 zip fleece I've had since 1996.

I wear it all the time. It's truly stunning how well it has held up.
 
Do you include shoes because I have some shoes that are at least 20 years old.
And ties? I have a school tie that's 45 years old (how British!)
 
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I have a couple of shirts I've worn since the early 1980's. And ties, don't wear 'em much any more, but one or two I've had since the late 1970's. I'm sure I have several more things from before 1990.
 
I have a really good cotton (and very stylish) raincoat that is one twenty years old, and which I remember my mother advising that I purchase, as she thought it an excellent (if expensive at the time, raincoat).
 
OG pair of Nike Air Flightposite B. I think these released in 2000.

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I've got a whitewashed denim heavy jacket my dad bought me for highschool, probably either 1988 or 1989.

There's a couple of Magic the Gathering t-shirts given to me by my sister's ex-boyfriend in '98 I believe that I still have.
 
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I have a pair of brown Levi jeans I got married in, so 22 years. Only fit for DIY these days. A leather jacket from the shop I worked in when I left school. I was 15 then. Thats quite a while ago.
 
I have some sweatshirts from College I have been known to pull out for Football games (or the dark blue one I wear when I climb under the house), I graduated from Auburn in 1986 and 1988, so they are that old, I have a Vandy sweatshirt from 1992 or 1993 I got for graduation. I wore my Pat Benatar shirt from a 1982 concert to the concert last year, Pat asked if it was real when she was talking to my wife and her coworkers after the show.
-Tig
 
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Hmm I’ve got a Star Wars Chewbacca Tshirt that my friends gave me in 94 er 95 ... caught my wife in it yesterday actually.

I have a pair of navy doc martens (with original rainbow laces) Ive had since 8th grade. Don’t fit anymore but figure my sons will rock them someday.

I’m sure I have more as I tend to hold onto stuff but I those are the first that come to mind.
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Oh duh, I’ve got my grandpa’s WWII navy man’s P coat. I love Pcoats. This one I’ll never get rid of even tho I’m kind of too fluffy for it Right now.

I’ve also kind of stole my big brothers Blue bass-master trucker hat. I remember the day he found it at Kings Island while we were waiting to ride the beast Rollercoaster around 86 er so.

He’s coming to visit in September so maybe I should wear it to pick him up at the airport:D
 
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I have an Arran sweater that my mother in law knitted for me 30 years ago. I only wear it for special occasions now.

Generally I have a small wardrobe and wear my clothes until they fall apart. I was checking our spending the other day and noticed my family of three has only spent £6.99 on clothes so far this year.
 
I work from home and only wear speedos.

Edit: *Please no more IM requests for autographed pictures will be honored.
 
An aunt gave me a Liz Claiborne crocheted teal and purple winter hat once, a soft and comfy one that I like and still wear when I'm shoveling snow. Think it's from back in the early 80s so it's definitely vintage Claiborne. I was shoveling my driveways by hand back then on my jaunts up here when I was still a weekend commuter from NYC... and I remember being grateful for the warmth of it pulled down over my ears in these Catskill Mountain winters. I still have that gratitude, even though I only shovel little pathways now to the driveways from the back door. Really comfortable crocheted or knitted caps can be hard to find so I'm hanging onto this well made one for life!
 
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