To a T When did T-shirts go from a celebration of individuality to just another ironic wink at the world? BY ALAN OLIFSON

I was at an airport a few days ago when a woman approached me. "Oh my God, that’s so weird, you went to Georgetown Day School?" she said. "So did I. When were you there?"

"I’m sorry, you must have me confused with someone else," I replied. "I never went to Georgetown."

"Then why are you wearing a Georgetown Day School T-shirt? It’s even got our cricket mascot on it."

"Oh," I said, with what I hoped was dignified finality. She continued staring at me. "Um," I added, helpfully.

She had busted me. I was indeed wearing a Georgetown Day School T-shirt. But I had never gone to or heard of or had any thoughts whatsoever about Georgetown Day School. I bought the shirt at a thrift store because I liked the colors and the retro design. And now here I was, face to face with an actual alumna. Not until this moment did it ever occur to me that Georgetown Day School was a real place, where real people went to school — during the day, apparently. The cricket mascot, its profile enclosed in a circle on my shirt, was also probably painted on the school’s walls and, quite possibly, existed somewhere as a mascot costume with an oversize head.

After I explained, with considerable embarrassment, how I had come to own the shirt, the woman walked off, leaving me feeling vaguely guilty. Like I had stolen something from her.

I had hit fashion rock bottom. When did it come to this? When did I resort to buying other people’s memories?

I’ve always loved T-shirts. But they used to be a celebration of my own individuality and personal experience. After all, I grew up in the golden age of the iron-on. I don’t know who invented the iron-on, but he or she was the Gutenberg of the clothing industry — taking self-expression-through-T-shirt down from the cloistered towers of elite silk-screeners to the people. At no time before in history were so many free to say so much with such a vast array of unicorns and rainbows.

My favorite iron-on involved the menacing caricature of a soccer player, eyes bulging with manic glee, kicking a soccer ball with superhuman force — said force indicated by a rainbow streak in the ball’s wake. On the back was my name in giant metallic letters. The shirt declared, "My name is Alan, I play soccer, and I kick the ball so hard, rainbows shoot out. Back the fuck off." I loved that shirt. Until I was walking to school one day and some high-school kids drove by and yelled, "Nice shirt, Alan!" My first thought was, "Damn straight it is," but then I realized what was going on. I may have only been 12, but I knew a mocking tone when I heard one. I never wore the shirt again.

But just because iron-ons were no longer fashionably feasible didn’t mean I was going to stop expressing my individuality on 100 percent cotton. I moved on to questionably appropriate joke T-shirts — the iron-on of the ’80s. A small sampling of my wardrobe: an obese woman calling out, "Henry, where are you?" to the skinny man stuck in the butt crack of her naked backside; the adventures of Captain Condom, which probably needs no further explanation; and, my favorite, Scumby — Gumby with a five-o’clock shadow, beer belly, cigarette, and a bottle of Jack. Simple, elegant.

Once I started college, and in the interest of possibly getting laid, I retired Scumby and graduated to a more mature form of T-shirt expression, i.e., the commemorative T-shirt. Instead of branding myself with displays of questionable humor, I now branded myself with displays of experience.

The most common was, of course, the obscure-concert T. Concert T-shirts were great because they answered the age-old question, "I know I’m cool for seeing Mary’s Danish tonight, but next week how will Wendy Baum in my Art History 2A section know I’m cool for seeing Mary’s Danish tonight?"

I never fully embraced the concert T-shirt, though. I mean, sure, wearing a shirt from an obscure band’s tour could feel hip, but actually waiting in line with a bunch of stoned losers for 30 minutes after the show to buy it felt more sad than anything else.

Of course, concerts weren’t the only thing being commemorated when I was in college. Silk-screening had really come into its own by then, allowing drunk college students to commemorate any event with a reasonably priced shirt. This meant the market was flooded with T’s depicting popular TV and comic-strip characters drinking out of kegs or smoking bongs.

After college, my use of T-shirts as expression began to wane. Partly because I wasn’t going to as many events that lent themselves to T-shirt commemoration — an image of Calvin and Hobbes trying to stay awake over the caption WEEKLY STAFF MEETING ’04 isn’t such compelling fare. Nor is ZACH’S BRIS, for that matter. Plus, in the workaday world, simplicity and versatility started trumping expression in my early-morning fashion decisions. "What does this say about who I am?" gave way to, "Does this match?"

Then one day I showed up to work in an outfit composed entirely of items purchased at the Gap, down to my underwear and socks.

Something had gone horribly wrong.

And so I hit the thrift stores, determined to reclaim my sense of individual fashion. But I made a mistake and gave in to trend. I should have stuck to the old thrift-store staple of obnoxious patterned oxford shirts and cheap jackets — items that let you mix and match and make your own statement. But I was seduced by the ironic vintage T-shirt, with its promise of prepackaged meaning and history. I bought Georgetown Day School.

T-shirts used to be about commemorating events we’d actually experienced, making the fleeting, in some small way, permanent. But now they’re just another ironic wink at the world — mocking the experiences of others in lieu of relishing our own. I fell for it once, but never again. I’m going to go back to making my own T-shirts, and I’m bringing back the iron-on. Anyone want a copy of my first one? It’s LAST ‘OUT THERE’ COLUMN OF 2004.

Send old T-shirts to Alan Olifson at alan@olifson.com