Mine is gear: a violet hoodie purchased when I was in the 9th or 10th grade (I'll soon be 29yo) . Me and my mom got matching ones for a trip up to the mountains for Thanksgiving. She still has hers too. I only wear it at home when it's chilly and I'm stubborn about cranking up the heat.

Non gear: I've got a bag with some classic favorites from around 2001-03. I've kept them in case I'm ever that size again. I keep flirting with that size but haven't quite nailed it (currently quite far from it).

Shoes: I've actually got a pair of oxfords an uncle bought me back when I was ...12 or 13? I barely wore them bc they were not cool at the time.....thankful these were well made shoes and I kept them. they will be making the circuit this fall. thanx uncle!

My wedding dress! Due to weight loss, I hardly have anything from the last year or two left.
My wedding dress is four years old.

I will say that I have a WMCA Goodguy Sweatshirt that I have never worn. It looks this http://www.whirlindisc.com/wmcagood.htm . I won it in a radio contest in the 7th or 8th grade. I had to enter a knock-knock joke to win it. So that makes it about 48 years old! My mom saved it for me. I have included a pix of me that I took of a denim on denim challenge--just so you know that I'm not as old as a dinosaur. Yet.

Gear: Umbro shorts, circa 1993. College sweatshirt, 1993.
Sentimental: My wedding dress, handmade by my aunt, 1996.
Still Wear: Black lace-up western boots, 1992.

Just about everything else dates to 2006 or more recently. My personal style makeover began in the summer of 2006 and I found YLF in the summer of 2007. I wasn't very good at choosing flattering clothing prior to that time!

I have a few,but a vest my mom made me in jr. high probably wins. Yup, I still wear it and love it ! It is about 35 years old !

Probably a few t-shirts from my freshman year in college: 1986. I keep them for sentimental reasons only.

Probably the item I kept the longest and wore the most was a beautiful knit wool suit that my mom bought for me when I was 17. It was (at the time) the most expensive piece of clothing I'd owned and it was the first time my mom had allowed me to wear head-to-toe black. The jacket was double breasted with small gold buttons and a v-neck and the skirt fell a good way below my knees (hey, it was the 80s). I wore the dickens out of that suit, eventually having the skirt shortened as styles changed. I felt grown-up and elegant in it, and it lasted until I finally called it quits. I loved that suit and I got every cent out of it:)

Isabel, I had a vest my mother made for me in junior high or high school too, and over the years I've wished I'd held on to it many times. It would be perfect right now, (despite being over 20 years old!)

I have a college sweatshirt that's over 10 years old that I still wear a lot, at least around the house or when I'm back visiting my old college town.

I have a few skirts that are about 5 or 6 years old that I wear and don't plan on getting rid of any time soon.

NK - that is so funny ! Maybe she could make you another one !!!! If yours were still around, it would be a "tween" next to mine !