I was dancing at Axis (Boston) one Saturday night in 1991 with that particular shirt on. During the next week, I heard Nick Carter, the disk jockey who had been working that night, talking about "dare to be different" on WFNX radio, where he worked during the day. Over the next month or so, the expression spread like wildfire across the country, to the point where magazines thought it was quite chique to say someone was "daring to be different."
At that point, all I could do is think "Gee, I wonder where that expression came from!"
Now I can sell you a copy of the shirt, if you'd like one of your own.
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