I hope you like looking at and reading about t-shirts buddy because holy shit there are a lot of t-shirts in here. I was wearing my almost twenty five year old Oasis t-shirt yesterday (and also today) and although I often wear it from time to time it all of a sudden transported me back in a way that it usually doesn’t. It’s also finally at long last starting to turn into a piece of shit and fall apart. I wanted to ask people about the oldest t-shirts they own and what they mean to them. Here are like fifty (?) of them. Sorry I couldn’t get everyone’s in this was already getting very long. Thank you to everyone who contributed.
This newsletter as you know is usually about a lot more political and depressing shit (although there are some really sad stories included below). Subscribe if you can to support my work please and thank you.
Violator tour 1990. My oldest sister bought it. It has since been worn by several members of my family, including my wife and my grandmother. I wore it every moving day between the ages of 18-30.
This was my dad’s shirt, but I took it from him in middle school/high school to be cool and vintage and edgy. My dad is a staunch Democrat and growing up we heard a lot about it. He made sure he’d never vote Republican again after voting for Reagan, and then the year I was born the bank foreclosed on our farm in Wisconsin. I hardly ever wear this shirt in public anymore. It used to get a few turned head or smiles, but now I hate it. The older I get the less of a moderate, farming-focused, middle-ground Democrat like my father I become and the more I want to burn the whole farm down with every politician locked inside. I haven’t thrown away the shirt because it’s not technically mine — and every now and then I see it in my closet and briefly think it’s cool to own an old campaign shirt — but then I remember that they’re all shitheads who have duped both sides of the aisle, present-father included.
The first picture is 2002. That’s my best friend Jimmy Proc, a Brockton firefighter who committed suicide in 2010. That’s my daughter Dani, she just turned 22. Yeah I had blonde fucking hair. Not in the pic, but to our left my mom was dying of cancer on the couch. This pic was taken at a cookout we had at her house. The last one we ever had. She died a couple weeks after this. 9/2/2002. And we sold the house.
Next is a happier day. 2014 Vans Warped Tour at XFinity Center. I dig this shirt out from time to time. It’s in a pile of black t-shirts I have stacked that are my “metal show shirts.” I love it because it’s old school and I just feel like me in it. I came of age with Tree, their music got me through some of the worst shit in my life, plus it’s a pretty “Boston” shirt, without screaming “Sweet Caroline” or sports, and Boston and its culture and its stories are a big part of me and who I am. Not gonna say bury me in it, but I wouldn’t be mad.
This entered my life circa 2010 but I don’t know how old it technically is because I found it in the rag bin in my friend’s basement when we were smoking weed down there and knew I had to have it… It’s the most successful tie-dye of my life and I stand by the sentiment that readers ARE leaders.
I found this Eric B & Rakim tour shirt, women’s small, at a thrift store in LA in like 2000. I ran into Rakim at the Rock Ready anniversary in New York while I was wearing it. He wrote “Rakim, Ani, Allah” on it in Sharpie. His signature has since faded away. I got it framed.
Over 20 years old from Roots Canada. Did we do it? Haha I think not. I had another one from Roots about the hole in the ozone but that shirt is long gone. As is the issue with the ozone hole??
Cypress Hill was my second ever concert (the first was a few weeks earlier, Aerosmith lol) and it was at the Armory in Philly. My friend picked me up (he had just gotten his license). He was like the coolest dude I knew (skater, in a hardcore band when I didn't know what hardcore was). When I got in his Explorer, I heard Rage Against the Machine for the first time and was like “What the fuck. where has this been all my life.” At the show itself I moshed my brains out.
For Quicksand it was at the Troc in Philly. It was Orange 9mm, Seaweed and Quicksand. Not even sure how I wound up there. I'm not sure who would have exposed me to any of those bands. I think we just wanted to go to a show. Of course Quicksand was incredible. Slip to this day remains one of my favorite albums of all time.
They all have really good stories, but maybe The Meatmen one is worth talking about. It was from a show at The Channel in Boston in February, 1988. I was 15 and had started going to all ages shows at The Channel the summer before. My first show was the Butthole Surfers, I got my mind completely blown, and nothing was the same after that.
The Meatmen's humor was perfect for a 15 year old boy. Tesco Vee came out at one point with a cardboard cutout of Elvis strapped to his body, stroking a giant double-sided dildo that he was covering with hand lotion and intentionally getting all over the crowd, who were then spitting on him in turn. Late 80s punk and hardcore was something else.
To this day I can't make any sense of The Meatmen to be honest. I loved them then, I love them now, but I am so horrified by the lyrics they shock me to listen to. It always felt like an inside joke at the time, meant to be inclusive, made by a guy who's a schoolteacher in “real life.” But they're horrifying in the current context, and I can't stomach them now, no matter what the intent was then.
This was my dad's 1997 Roger Clemens Toronto Blue Jays t-shirt. My dad died in 2016. I took care of him for the last 2 1/2 years of his life, and though the overall experience of doing so was transformative — it gave me a chance to work all my shit out with him before he died, which was a gift — the reality of it day to day was brutal. It's not just the dying slowly part, it's things like cleaning up literal shit from the floor when he fell out of bed and having to pick him up like a baby and carry him back to bed and listening to him cry because my brother wouldn't visit him for the last months of his life while confined to a home hospice bed.
After he died it fell to me to clean out his house. He had hundreds of t-shirts, mostly of various places he'd visited (he was on the road a lot) and silly stuff like the shirt with holes in it with a big “WHO FARTED” iron-on graphic. There were only two that I kept, this Clemens jersey that he got at Skydome in Toronto, and a Calvin & Hobbes bootleg shirt featuring Calvin pissing on a Yankees logo that he bought on the street outside Fenway. I didn't send a pic of that because it's in the laundry — I wore it to the gym the other night to piss off my Yankees-loving friend.
Anyway, I kept them because I got my love of baseball from my dad. When I was a kid, he took me on the road with him a lot and always listened to Sox games on the radio during the season. We went to a lot of games at Fenway together as well. The shirts remind me of those days. I don't have a lot of happy memories from my childhood, but those trips to Maine and New Hampshire, delivering merchandise to customers from his van, are ones that I cherish. These shirts are tangible reminders of him and those days, and that baseball was one of the few genuine connections we had. Sorry if this is longer than you'd expected but it's August and my therapist is on vacation.
Yes, it's a commemorative Zoot Suit Riot t-shirt. I can't be certain but it's got to be 1997 or 1998. I know that swing revival gets a lot of flak for being corny, but in 1997 I was in high school and we didn't have a computer, much less the internet. When you heard a song on the radio you either liked it or not. You didn't hop on Twitter to see a zillion people dragging it. So anyway, in that context, I heard Zoot Suit Riot and thought it was the coolest thing in the world. My group of friends didn't really have strong music opinions, or at least we didn't discuss them, so no one talked me out of it.
I lived in that thing for probably the better part of five or ten years. I'd bet I haven't taken it off the hanger for at least ten. It just hangs in the back of the closet and I scowl at it every time I'm trying to reach back there to get my one suit out.
I went from swing to nu-metal, neither of which were broadly popular choices at the time. Maybe a year or two ago I think you linked an article in defense of nu-metal and the whole time I was thinking... when will they write this for swing music?
The Cherry Poppin' Daddies actually played Worcester in November 2019 at that snooty piece of shit beer garden. My high school buddy flew up here from Missouri and we went and saw them. I was not aware the lead singer is no more than 5'3". The visit was a little unsettling. My buddy is married and has three kids that go to dance recitals and he doesn't drink eight beers a night and shitpost on Twitter ten hours a day so it was like a brief glimpse into an alternate reality.
Hi it’s me Luke for this one. I’m not flexing there by the way my arm just did that by accident. Here’s my Oasis t-shirt. I must have gotten it in like 1997 or 1998 when they played in D.C. when I was an intern at the White House lol. I’ve shared this story in here before but here’s what I was up to at the time.
I hated working there very much and I hated wearing a suit in D.C. in the heat even more and I pretty much hated everything besides going to see shows at the 9:30 club. Most days I would fuck around on Lexisnexis which was a magical thing to exist back then in the nineties you could look up so many magazine and newspaper articles on the computer holy shit. Then you could print them off and go take a shit for like thirty minutes or jerk off or whatever you had to do down the hall from Al Gore.
Eventually I met a nice woman who was much older at the time I think twenty seven which I remember thinking was an insane age to be and she had a young daughter of her own whose name I will never forget because her name was Peaches and I’m pretty sure this was before Peaches was a thing. I’d go to AA meetings with her due to she was sober and I was too but not in the same way mostly because I had barely even started drinking at this point in my life which is in part because I was young but also in part because I always grew up being scared I might turn into an alcoholic due to [gestures at the entire history of my family] and boy was I right about that because I eventually did whoops. She had a friend named Fire I remember that too. Fucking Fire man. What a guy.
I interned in the press office at the White House and it fucking sucked and I hated being around nothing but southern sorority girls and ambitious nerds from like Ohio and I just wanted to go see Our Lady Peace or whoever play a show which is what interested me chiefly at the time. On the last week of my internship whoever my boss was some George Stephanopoulos underling asked me to photocopy what I remember being a whole lot of pages. I started to do it and then I said I’m not going to do this and I walked out and never went back.
I ended up getting a D+ for the entire semester since my grade was supposed to be doing the internship and writing papers about what I learned and such at the internship but I didn’t learn anything at all and I never will.
Anyway Oasis ruled then and still do.
The oldest t-shirt I own is an extra-large Soviet Era propaganda shirt of Yuri Gagarin saying “Payekali!” I got it from my arch conservative father by telling him that an actual communist should have it. Despite being a weirdo republican, he really respected the shit out of the space race and was always a big science guy. The shirt is older than I am and going strong. Good Russian Fabric. It’s from before the Soviet Union fell, that’s the best I can gather.
Scored from the AC frontman himself in exchange for a few lorazepam to “take the edge off.” The backstory is that Seth found an AC cover band in Russia and booked a tour with them as the opener. When he arrived, the fake AC came to get him at the airport. They were confused that he was the only AC member at the baggage claim until he asked which dude was the singer of fake Russian AC. “You? Ok now I’m the singer. You’re the roadie.”
I bought this t-shirt at the Ween show at Bogart's in Cincinnati on the Mollusk tour in 1997. It was my second or third time seeing them. My friends and I got to shoot the shit with them a little after the show, which was pretty cool. I somehow managed to never lose this shirt or snag it on a nail or screw it up in the laundry, so I've kept it and still wear it probably once or twice a month when I notice it in the drawer. It's a cool looking shirt that's held up amazingly well, and it's become a nice reminder of a really great year to be honest, which, come to think of it, was exactly half my life ago!
This is my RoboCop Converge shirt from around the time of Axe to Fall, 2008ish? I used to have a ton of Isis (the band) and a few These Arms Are Snakes shirts, but I lost just about everything I owned in a fire in 2011. Thankfully I was wearing the Converge shirt that day!
I've had a Ghostbusters t-shirt for 22 years. I got it at the Framingham, MA Salvation Army, and have pictures of me in it from every band I’ve been in. I almost exclusively wear it for special occasions because I'm afraid to wear it out too much. It's definitely a prized possession and I worry about the day it's too tattered to still wear.
This shirt is from one of my dad’s races and is probably 40 years old. My dad used to race dirt bikes in the late 70s and early 80s. My mom would go to his races and heckle him if he was behind. I found it in my teens and wore it constantly. I only stopped once it started ripping. I love this shirt and should probably get it framed.
This Quasi shirt is still my all time favorite shirt from Fall 1998(?) when they toured with Elliot Smith. We saw them in Providence? The Bethel Cross Country Invitational is from 1993 or 1994 (which for some reason feels like eons before the Quasi show). The long sleeve T was such a staple of cross country meets and it reminds me of feeling like part of a team.
I got both of these when I was 17 when I got my first car, a Ford Tempo. One of the first things the Tempo freed me to do was go to the thrift store and buy freak clothes to wear to school. I am from Camden, South Carolina, which had very few hipsters, so I felt a lot of ownership over my sartorial choices.
In 5th or so grade in suburban Chicago, we went on a field trip to a t-shirt making shop for some reason where we were kinda taught how the whole die and steam and whatever processes. Now that’s all lost to me. I think the t-shirt guy was a friend of the teacher or something. Anyway, at the end each of us was given a t-shirt. I think we could maybe pick from two options. Here’s mine. It still fits.
I have a Weezer one that is signed by everyone but Brian Bell. One of their first shirts, wore it all through high school and college too. Stopped wearing it after they signed it of course. My brother went to that secret show they played at the Beachcomber (on the Cape in 2001) and smuggled in my shirt to get signed. They were only supposed to sign one thing. When Rivers saw my shirt he goes “Whoa, old school. Tell your brother to keep on rockin!”
I still have my old 1992 “dream team” gold medal t-shirt with the cartoon heads. Laettner looks amazing.
My oldest t-shirt is from the 1986 Red Sox playoffs run. It says “All the way in ‘86” on it, and by this point, it’s so threadbare it’s almost transparent. I don't wash it anymore because I'm afraid it will disintegrate. It was my dad's, and I found it in a bag of clothes he was going to donate about a decade ago. I just loved the unfettered optimism and the dramatic irony of what would come during that playoff run. Pretty perfect Massachusetts doomer sports energy. You can see my nips through it though, kinda gauche.
I purchased this with my first paycheck in 1987. Actually I think it was earlier. I was a stock person at Pier 1 in suburban Chicago. Who could have guessed this teen was bisexual?
Bootleg I bought from the record store I worked at in 2000. A local guy made them. I was arrested in it at 19 in 2005. The cop that was booking me said, “OH! That’s cute.” in a pissy voice while looking at it. I sewed it up to make it tight, but have since unstitched to make it fit.
I have an original Black Flag My War shirt from 1985/86. My band Beartrap was playing a basement in some kid’s grandmother’s house in Eau Claire, Wisconsin. The whole basement was decorated in 80s punk/hardcore shirts, and I asked the kid if they were original. He said “yea my uncle grew up on all of it,” and he took me upstairs and showed me all this super rare vinyl. We went back downstairs and I asked him how much for the Black Flag shirt and he said “I don’t know man I don’t really wanna sell it ask me again at the end of the show.” It is paper thin/see thru white and it looks like someone painted a house in it, so it’s by no means pristine but it’s sick. The show came and went and it was a cool show. We said our goodbyes and as I was climbing the stairs to exit and leave I looked back and said “how much?” And he said “I don’t know $10?” and pulled it down off the wall and handed it to me!
I bought it with my Gap Outlet employee discount in 2006. It reminded me of M*A*S*H. Now I wear it as pajamas. Not cool but there's the truth.
This is my favorite shirt. I’m 47 now and I got it at the original Newbury Comics when I was 16. It was my lucky shirt. When I bought it, I was an ex-gifted kid fuckup on my way to dropping out of high school and giving up on life. A few chance events later, I was a freshman at a school I never dreamed that dirtbag girls like me got to go to. I was wearing this shirt for every one. I never wear it now. I live in Austin, and whenever people see it, they say, oh cool, Beto’s favorite band!
It's a little disingenuous because it's not the shirt that's been in my possession the longest, but the oldest shirt I own is a Shawnee Mission West High School football workout t-shirt that used to belong to my ex-fiancee. She stole it from some older boyfriend type back when she was, I believe, in middle school, but it ended up in my drawer because she liked how it looked on me. To this day she's pissed that she left it behind when she moved out. It's literally completely see through. I'm wearing it now and you can see all my tattoos and so forth right through it. It's got like 3 shirt molecules in it total.
I stole it from my best friend when I was 14. It was vintage then in the late 90s. It must be 50. It has never left my wardrobe.
Because I want to be the really old dude at the show.
An ex-girlfriend gave it to me about 20 years ago. I kept it because of Less Than Jake. And it says “Tehteekaxah”...so I guess I'm still mentally 16.
This warped tour shirt is now the same age I was when I bought it. Lotta people talk like they’re too good for post-90s Warped, but 2004 had a great lineup (Taking Back Sunday, Yellowcard, New Found Glory, Coheed, Bad Religion!) and was maybe the last one where Yoohoo was the big sponsor and you could opt for free chocolate milk instead of $8 water.
A My Life with the Thrill Kill Kult shirt from when I was 12 that I kept from the older girl I lost my virginity to during a satanic death spell she said she needed a virgin for so she could kill her best friend whom she thought stole her KMFDM cd. Turns out she had just left the cd at my house and it was like under my bed. The shirt originally was one she stole from her boyfriend at the time but cheated on me with because he was not useful to her in the satanic death spell as he was no longer a virgin. Circa 1996 Florida. I left the shirt at my aunt’s house around that same time and forgot about it, only to be reminded it of it sometime in the mid 2010s when she was unpacking some stuff. Now that I’m much larger, it fits like normal.
Maybe not as old as others, but mine is this Beach House 2012 tour shirt. It is still one of my happiest memories. I went to Pittsburgh for the show. Cried a lot. Got the drunkest I've ever been after with Canadians from my hostel who'd come for the show too. I was so hungover the next day I puked in a diner bathroom. (Still feel bad about that.) Still wear it a lot despite underarm stains.
The oldest t-shirt I own is a baby blue Ugly Casanova shirt that was the first thing I ever ordered online in 2003, after some Dragon Ball Z tapes my dad got direct from Japan in 1997. When it came it was a size too small and I was a growing, already really big for my age dude, so that first day I took it as a sign and made it a ‘goal’ shirt and started running. I think I tackled like 6 miles that first night. Started my transformation from lumbering catcher cleanup hitter to leadoff center fielder over the span of a couple years and got down to a size medium even as I aged from 12-16. I still wear the shirt in my regular rotation at age 31. It’s kept me honest whenever I’ve started to gain weight.
First concerts I ever went to in 2005 and 2006. I’m definitely never going to fit into a medium ever again but feels weird to get rid of.
This is the oldest shirt I own that I still wear regularly. Bought it at the Echo Lounge in Atlanta, GA in November, 2000 at a How Water Music/Alkaline Trio /Strike Anywhere show.
I was a baby during this tour but my parents were not and I inherited this and a pair of steel toe hiking boots from my dad. My dad and I don’t get along, but we do connect on movies and music, and while neither of us are big Huey fans today it reminds me we can still have a conversation before it careens into an argument about which entities are responsible for destroying the world.
Oasis tour shirt purchased off of eBay in early 2000. (Thank you Mom for letting me use your credit card). Men’s size large but I wore this to 6th grade regularly and got teased mercilessly. The other girls my age were very into Britney, Christina, etc. and I was all “Hey Noel Gallagher is really cool.” But here we are 20 years later and I am still supremely into this shit.
Aaaaay! My The Fonz shirt must be from the late 70s.
I got this one when I saw him on the Odelay tour at Lupo’s in Providence in August of 1996. My first concert.
Check out this Tuesday shirt. Looks like shit now but she were something in her day.
I was a douchey jock in high school and college but in 1999 I almost died of pneumonia. I was on ventilator for 5 weeks, all fuckedd up. Back to school the following year I felt like my identity was gone. I was kinda lost. I really latched onto Get Up Kids, Sunny Day and especially the Chicago bands. This shirt encapsulates a bit of that.
1994 Rolling Stones Voodoo Lounge tour. I was in high school, parents getting divorced. One of the first times I remember doing something with just my dad. It was a blast. We went back the next year for the Bridges to Babylon tour in 1995 at MSG. Still got that shirt too. Not even much of a Stones fan, it was just cool to see the legends play and go with dad at that age.
U2 concert tee. Unforgettable Fire tour. August 1984, Wellington, New Zealand. My first big concert. Ticket was $20nz. Obviously the tee is out of rotation now as it is fragile as hell. It sits in a wardrobe, just getting older.
I still have an absolutely brown t-shirt that my dad bought for me at my very first concert. Like many young people, I was a Dylan obsessive, and when he came to Atlanta to perform at the legendary Tabernacle, I convinced my parents that I had to go. They were nervous about letting me drive two hours into the city to park downtown, but they knew this meant a lot to me, so my dad decided that it would be a thing for both of us. He bought tickets, and we drove to Atlanta, and I saw Dylan (this was one of his off-nights.) Also, I was a naive sixteen year old and my dad sort of waved away my questions about what that particularly funky rope-burning smell was wafting from the area near the stage. But I still have the t-shirt. And my biggest memory of that night is from before the show. My dad took me to Ruth's Chris, which had to be my first visit to a really nice steakhouse, and so I keep the shirt not because of my affection for Dylan, or because it fits — it doesn't and every time I've tried to put it on since I was 20 is a cruel reminder that I'll never have the lithesome body of my teenage years. It's almost a mockery now — but because that was the night that my dad decided that I had to know how to handle myself at a Very Manly But Also Fancy Place. So that's my oldest t-shirt. It's from the night my dad decided he needed to make sure I was never going to look like a rube.
Here’s my Pearl Jam Alive or Stick Figure shirt from 1991 or 1992. Probably bought it at a record shop in New Hope or Doylestown, PA, which would mean either Spinster’s or Siren, respectively. Spinster’s is long gone, but Siren is still kicking. I wore this shirt most “dress down” days we had in my Catholic high school. That it still fits shows how large we wore clothing in the 90s. This band was, for me, a pretty typical story: sad, teenage, classic-rock leaning kid gets his mind blown by (mostly) Eddie Vedder and his antics and the slick drummer and the backstory. It was having a fresh driver’s license and somewhere to blare Ten on repeat and rage. It wasn't my parents' or older friends' music. And sure, it was a Personality Type—“Pearl Jam Guy”—for a while, too, till I grew out of that (and became Sunny Day Guy). But they were a real awakening for me. They changed the way I thought about music, brought me closer to my brother (we played music together for years after this), and introduced me to tons of underground bands, progressive values, and life-long weirdo friends.
I saw Buddy Guy with my dad in 2000 and a detail on the shirt that I always thought was funny is that on this tour he wore a billowing silk polka dot button up shirt that matched the guitar and strap, but on the picture on the shirt he’s just sporting a flannel. I got to see a few of my dad’s blues heroes with him while they were still touring in the late 90s and early 2000s and now I blast Chicago blues to annoy my children. Time is a circle.
This is a t-shirt from an off-season wrestling program I did that dates back to probably 1998-99. I never had much luck with sports. Lousy baseball player, passable basketball player but on the shorter side so nothing doing there. A buddy and I tried out for the wrestling team on a lark. I was interested because I would rent UFC videos on the weekend and back then being a good wrestler seemed to mean being able to kick ass, or at least not get your ass kicked. Probably I was never much at risk of getting my ass kicked, but when you're 14, 15 years old it feels like an ever-present threat. Anyway after I showed some promise freshman year (our starting 119-pounder got mono so I had to replace him in districts) I started going to this place in the offseason to accelerate my development. I did get better, by my senior year I was ranked 5th in my weight class in the state of VA. Funnily enough the closest I ever got to getting my ass kicked was there, the gym cleared out for a break and an older teammate held me back and kind of roughed me up a little because I said his girlfriend's sister was ugly. Pretty sure the coach knew it was happening.
My softball coach gave the red one to me one game when it was chilly at the field and said keep it. My family did not shop at the Gap in the 1980s, so it was like my prized possession and probably the only name-brand item of clothing in my closet at the time. The scrub shirt is from St. Margaret’s hospital in Dorchester, which has since closed. It’s from 1987 when my youngest sister was born. I think my dad had to wear scrubs because my mom had a c-section. I wear it to bed at least once a week.
Now I’m slightly horrified at the number of clothing items I have and wear that are more than 20 years old.
Here’s my 7th grade track and field t-shirt from 2005, from the private Baptist school I went to where we learned young earth creationism from homeschool textbooks and I got suspended for setting stuff on fire in the bathroom, which was bullshit because I did it safely over the toilet. It was a medium and way too big on me then and now it is too small but I still wear it because it is magically soft. I think it will probably last forever. My wife has started stealing it. I wish I knew what it was printed on.
My oldest shirt is one my dad gave me when I was maybe sixteen and I think his parents gave it to him in the 1980s. The shirt advertised the “Ames Plow Boston,” which I think used to be a restaurant in Faneuil Hall that closed in 2004. I have no idea if that’s when Faneuil Hall started to suck or if it always sucked but you still want to go to it for some reason. I think my grandparents went because my dad was born in Ames, Iowa, but I got the shirt before I knew myself that I would go to college at the good old Iowa State University and way before I knew that I would eventually move to Boston. So now I have a shirt that somehow represents both of the places I have spent the majority of my adult life. I like to think I moved 1,200 miles from my hometown because of a shitty bar t-shirt.
My contribution is a Discount (the band) t-shirt from 1998. The back story is from their tour in the same year. They had an open date where a Detroit show would fit perfectly. So we booked them and promoted the show. The shitty pop punk band I was in at the time sucked at promoting gigs and nobody came. Discount couldn’t have been more gracious though. They cracked jokes about nobody being there because Assuck was in Detroit at another venue the same night. I felt really bad, so I spent money on all of their merch that I didn’t already have. This shirt, which I still have, was among the merch. I wear it a little less these days because I don’t want it to fall apart.
My oldest shirt still in semi-rotation is a Pink Floyd “hammers” shirt (from the film version of The Wall) I bought as a college sophomore in 2005. I don’t have a lot of sentimentality about it, despite Pink Floyd meaning a whole hell of a lot to me back then. I still love them, but ya know, it’s not the same as it was. I’m guessing lots of us went through those phases with Zeppelin, The Who, etc. when you can finally buy (or pirate) your own music. Or it could’ve been I worked in a dining hall kitchen in college that had classic rock playing 24/7 so now I am good on anything considered classic rock for the rest of time. I only hang on to it because remarkably the screen printed stuff hasn’t cracked to hell or faded miserably, but I generally only wear it for working from home or walking the dog, etc. I’ve included a pic I found online of the shirt but not my shirt, but it basically looks the same.
I'm a t-shirt hoarder. Here’s a Slayer shirt that I bought at the mall in 1988. I wore it while playing at The Grove in Anaheim in 2007 when Deadly Sins opened for Dropkick Murphy’s. I love the Slayer Live album from the Grove 2002. I also have an REM shirt from 1989. I bought front row center tickets for $75. The best seat in the house...$75. The other is a Replacements shirt from 1987. This pic is of my very first show in front of people. However, the shirt was white and died a horrible death. I was crushed. A few years ago I found a reproduction and immediately felt like that kid from 1987 all over again.
One of my oldest shirts is a Shiner shirt that is just a ripoff of the classic Slayer shirt, absolute favorite of mine, cracked to hell.
Bought used at the AmVets on Comm Ave (?) in Allston circa 1999. Years later I wore it to a bar and my finance bro buddy told me I’d “never get laid wearing stupid t-shirts like that.” Next time I wore it I met my wife. I can’t get rid of it, but when I do it’ll be a sleeping shirt for our 12 year old daughter. It doesn’t smell so great anymore.
I don’t know how far your definition of t-shirt goes, but my oldest is the 1991 shirt from my hometown footb…soccer team Aberdeen FC. Everything about it: the team, the early 90s, the style, is incredibly lame, but I love it.
I don’t know if anything says washed dude from Boston like occasionally trotting out a Sam Black Church t-shirt in 2021. I still remember when their stickers were ubiquitous in Boston, now I’m looking at posts about reunion shows and wondering how they couldn’t get Honkeyball on the bill.
I have a 15 or 16 year old Cobra Custom Tattoo t-shirt. It’s black with gold lettering. It’s beat to hell with rips in the shoulder and the bottom seam is coming off. The back of it has at the top “Cash, Grass, or Ass, nobody rides for free” and the location and phone number of the shop.
It is the quintessential rock n roll t shirt. I got it from my roommate who tattooed there, and he put a giant cobra on my chest. It’s probably the greatest t-shirt I have, and I love my t-shirts. I can’t wear it too much or it’ll completely disintegrate. But nothing lasts forever.
My mom got me this for my 13th birthday. I always felt out of place with other kids at school because I listened to rock and punk instead of rap and pop, and this was one of the first things I owned that I really felt like expressed myself and what I valued.
I got a Lupo’s Heartbreak hotel t-shirt with the original address and The Cars Door to Door t-shirt from my evil stepmother whom I was first introduced when she slashed all four of my mom’s tires when my dad was taken to court for not paying child support. I got the t-shirts after my mom kicked me out after a decade of heroin addiction. I lived with my dad and step mom for one day, got the t-shirts, then they called the police because I was doing heroin in the basement. I kept the t-shirts though. I’ve since never talked to them again So worth it. The Lupo’s is worth so much money. I’ve got a lot of trauma connected to t shirts lmao.
I “won” a WBCN radio contest to see the last showing nationwide of Gigli. I forced my girlfriend to come with. I think it was at the Fenway theatre in 2003. Good time, fun atmosphere. Recently dug it up. It must be peaking in value with the emergence of Bennifer 2.0.