The teachers even got in on it.
The Hawaiian shirt is a controversial piece of fashion. People who live in Hawaii know how to wear them with taste and they are welcomed at almost every occasion.
Off the island, they are usually worn by two different people: rich dudes who wear $125 Tommy Bahamas to show they can be chill on the weekends or the drunk frat guy who picked up an obnoxious one at a thrift store.
Then there's writer Hunter S. Thompson, who's loud choice in fashion equally matched his flamboyant lifestyle.
In 2016, Dave Husselbee, a junior at Sleepy Hollow High School in Westchester, New York, got five of his friends together and bought five loud Hawaiian shirts to wear on picture day. The idea was that the ugly shirt would be a running joke throughout the annual.
"We bought five shirts and about 10 kids knew about it before picture day," Husselbee told ABC News.
Other kids who lined up to have their photos taken loved the idea and put on the shirt as well. Then, some of the high school staff got in on the joke. "Some of the staff was unsure but once the chair of the science department decided to do it, all the others were enthusiastic," Husselbee said.
All in all, sixty people wore the shirt in their yearbook photos, turning the solemn pages into a sun kissed island-style daydream.
The school's principal, Carol Conklin-Spillane, thought the prank was a great expression of the school's fun-loving spirit.
"The best part is that this is who we are here at Sleepy Hollow High School," she explained. "Kids and teachers have wonderful relationships. It's a very warm, wonderful place. That's really what's special about this place. It's an example of how these four years in a person's life can be transformative. It's all about the relationships these young people have with adults."