While they're vaguely iconic, Hawaiian shirts are, at this time, basically impossible to pull off; even if your interest in them is strictly ironic. The only way you can possibly do it is if you are Wilford Brimley and you are in a film called "Cocoon" - which you will have to time-travel back to 1984 to make.
I have always loved Hawaiian shirts I was given one by my grandpa one once. And had several throughout the years I liked them for the comfortable wear they provide. As I really hate the heat anything above 80. So yeh I would rather be cool and look like tony soprano on vacation than be hot.
Cheers
I still have some. I'll rock 'em without qualm. mainly in an ironic manner. go ahead and call me on it, I'll laugh too. and keep rocking it if I wear it out of the house.
I used to have to attend mandatory fun events after hours. some of us made a game out of it and ran an "ugly shirt contest" amongst ourselves, behind the boss' backs. some of the bosses'/more senior's wives thought we just had atrocious taste. most of us simply played stupid, and asked what they could possibly mean, "I love this shirt!". so we had fun with it.
I live in northern Canada. I own a thick parka, a shearling bomber hat and felt-pack boots. They keep me toasty warm in -30 degree blizzards, but look darned silly if I try to wear them anywhere else.
Hawaiian shirts ... look great in Hawaii, but ... and you can probably see where I am going with this ... absolutely foolish anywhere else.