For me, its the jeans that my friends and I deconstructed ourselves by using razorblades to wear down the fabric, bleach to do splatters and designs, and sometimes even paint to give it a little extra wear and love and individuality. Apparently, thats not been a thing since the emo days.

Everyone is wearing destroyed jeans here. o.o
I had this pair of All Stars White converse shoes, with silver stars on - they lasted a long time [and they were on sale too, i think?] i eventually had to throw them away because they were coming apart T-T i still miss them. I got a new pair of Converse shoes, really comfortable, with animal print, but they're just not the same thing, HAHAHA I can't think of anything else i really liked and now miss.
I used to wear denim overalls all the time as a kid. They were super comfortable and just felt nice to wear. I wish I could get away with wearing them now. :(
I also had a few comfy sweaters and sweatshirts that I used to wear that I miss.
So many people in this thread have said that worn/torn jeans aren't in style. Maybe it's just the area I live in but they've been sold in shops recently and I see plenty of people wearing them so are they not still "in style"? Not that that kind of thing is actually important...
Just lost a pair of bamboo shorts a month ago. Would wear them everywhere during the summers. Jogging, hiking, camping, clubs, rolling around in mud, swimming, sleeping when they're clean. They went through a ton of hardship for over 6 months each year. Had them for three years. Actually contemplating sewing the ripped bum to keep them alive for longer, but have no experience with bamboo clothing.
Worst part is the company makes new designs for their cloths every year. So even though I do enjoy Nomads and their cloths, I have not been able to find a pair of shorts that fit so well. Plus, 60 bucks for a pair of underwear this year? Will wait for next years line, thank you! (It's seriously sold as underwear...)

Okay, I'm probably going to sound super dumb for all of these
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I always have been and forever will be a fan of low-rise bellbottom jeans. I had a bunch of them when I was in high school but my weight changed a little and I got rid of my jeans... well, now I can't find them anywhere... I'm going to keep checking at Ross but I used to get them from Hollister. And if I had kept my jeans they would've fit again by now, so that's really my own fault :'(
I am SO NOT into the high-waisted/skinny legged jeans that are out right now. Please, bring the old ones back!
I had this long stretch denim coat that buttoned the front and I loved it to pieces. Grew out of it eventually and I wish I hadn't gotten rid of it.
[egg=TheGeek] [tp=TheGeek]
i miss a pullover but he was old and really damaged when i put it in the trash
My jackass arm cuff. XD I use to wear this when I was a Gothic kid back in high school.
I may have not been born in that generation but boy do I envy those bell bottoms and angel sleeve shirts that were popular in the 70's. As well as the Mod fashion. However since I've always loved the clothing style of the 40's I'll have to choose that as mine. Soft spot for a well tailored outfit. . . I say like I have the money for a nice tailored clothes. (In my defense I have one really nice dress that's tailored and have an appreciation for seamstresses because my mother was one.)