I've got an Ocean Pacific thin oversized t-shirt that I got in sixth grade. That was back in 1986 or so? I still wear it as a sleep shirt and sometimes as a cover-up if I'm wearing a swimsuit.

I no longer wear my HyperColor shirt from eighth grade, as it has tons of holes in it.

I have a long-sleeved pocket tee that I bought in 12th grade (end of 1990) that I will still wear on occasion.

The funniest thing was going to my uncle's house the other night-- my cousin's youngest daughter was wearing one of my cousin's shirts from circa 1975-- her mom kept all of their shirts, so now her daughters can wear some of them. Very cool since the retro screen-print and iron-on look is back.

32 years ago....
 

I wear my mother's Ralph Lauren Polo shirts that she got when she was my age: 32 years ago!! I also wear the first cashmere sweater she bought the same year all the time. Both items still look new!

I have a T-shirt I got in 1st grade (1986-1987) I still sleep in.

I have a pair of boots that were a gift to me for my 14th birthday. They are soon to be 10 years old.

I have a black tshirt that I bought in 1988. Anywhere remember Au Coton?. The color has faded and has some spots that were a result of wearing it when I painted. It's comfy,soft, and I'll wear around the house or out doing errands.

I have a pair of Doc Martens that I got when I was in the 6th grade. That was back in 1991. The still look good but if it rains, the water leaks in through the bottom.

A dress from 1888. I wear it for special occassions at church.
:)
Silver

My friend Jenny has a very similiar one! ;)

I have an "Arrowhead Basketball Camp - 1994" that is the oldest one I still wear on a regular basis but I have some old shirts of my dad's that are older, including his army uniform. :)

When I was in Middle school, I "stole" my dad's blue zip up hooded sweatshirt that he had from when he was in college. It was just hanging in the closet and it obvioulsy didn't fit him anymore. It fit me though, and still fits me now, 10 or so years later. And it's in great "well-worn" shape, considering its got to be at least 30 years old. No holes, zipper still works. It's just slightly, oh so slightly cause it is STILL dark blue, faded.
Amazing!