Well, I guess I'll get this thread started off, although I was kind of hoping someone else would.

Old Fit Pic:
This is a German military field jacket I found at a Buffalo exchange on Haight street in high school. Whoever owned it before me put some darts in the back and added a vent, so it's pretty fitted on me, although probably a little too short in the sleeves and the body. At the time, it made me feel good. This is one of the first items of clothing I picked out for myself, and I've held onto it longer than I've held onto any other clothing I've owned. For probably four years, this was my only jacket. Day in, day out, this is what I wore in high school. I wore this at the beginning of my freshman year of college, when I got together with a few people and got really drunk at a beach, and then ran around the city, sat in an art gallery on a couch for about half an hour, danced in front of a busker at a pier, sat in a circle with friends on a wharf scratching each other's heads, ran after a friend running up a hill trying to "beat her asthma," and then playing foosball in our dorm while one of our friends fell asleep under the table. I wore this when I got really drunk and fucked up my foot falling off a park bench, while sitting on it (I think most of my stories with this jacket are drinking stories...). It's also the jacket I wear whenever I go out to shows. So I was wearing this the time Matt Berninger threw wine at the entire audience and hit me with some of it, and then subsequently shambled through the crowd right past me. Wore it last Friday going to see College, where someone asked me if I had a denim fetish.
Also, a quick note on the hoodie that's always layered with the jacket. That's because the jacket arms are too short on their own, and the hoodie has a giant blue paint splotch on the back from when I finished painting my current apartment and backed into a wall trying to take a photo.
Anyway, as much as I do remember, there's a lot that I feel like I'm forgetting. But for four years of my life, this was
my jacket. Putting it on was the last part of my morning routine. It's gotten beaten up quite a bit, and now I only really wear it when I go out to shows or plan on drinking heavily. Can't bring myself to get rid of it yet, though.
Looking forward to seeing other people's sentimental items!