True story, I used to wear Hawaiian shirts almost exclusively.
It was during the "Foundations" year of my art school days. The first year, in which each student was on a level playing field, and we all had to take the same classes. These classes were meant to introduce us to the various disciplines in which our art career could take; sculpture, photography, illustration, fine art, etc. It was meant to be a tool to help us choose a major and ultimately seal our fates.
Each of my fellow freshmen came to the art institute as the top artist in their graduating classes in our high schools, or at least they were considered to be "The Artist" among their peers. They differentiated themselves further by dressing the part, in what seemed to be the unofficial "uniform" of the art student: black shirt, black pants, boots, black nail polish, multiple piercings, tattoos, hair coloring, pasty white skin, sullen expression. At their schools, they stuck out and were considered "different".
Problem is, when they arrived at art school, they all looked the same. It was the great equalizer. No one stuck out. Not one.
I didn't want to be the "Death, skulls, blood, anger" type of artists that they all wanted to be. I wanted to draw cartoons and concentrate on humorous illustration. I had no desire to fit in. I wanted to stand out. So among all the sullen, black-clad mopes, I decided to be the antithesis. What could be more opposite all black, but a Hawaiian shirt?
So I started to collect them and wore them every day to school. I had all different types and colors. And stand out I did.
Needless to say, everyone hated me; and the feeling was mutual.