I love this, but don't you wonder how this started? Maybe he accidentally wore the same thing 2 or 3 times and decided to pretend it was intentional, then kept going.
Update: Dallas News had an article on this last year:
In every school picture for the past 40 years, Dale wore the same 1970s-era polyester shirt and coffee-colored sweater.
It began as an accident — a product of his sparse wardrobe back in the day.
“I was so embarrassed when I got the school pictures back that second year and realized I had worn the very same thing as the first year,” said Dale, 63.
But his wife, Cathy, dared him to do it a third year. Then Dale thought five would be funny. “After five pictures,” he said, “it was like: ‘Why stop?’”
via @_you had one job