Yeah. Seems like it may only work when you’ve got yourself all lathered up in smugness like this guy. I couldn’t do it. Especially since my Grandma was known around our family for her love of her favorite Bolivian poncho my uncle gave her sometime in the 1970’s. Too strong an association for me to overcome.
I'm continuously told that I can't wear a keffiyeh/shemagh as a scarf with my pea coat. I do it anyway. It was a gift from a friend from the middle east and I think of him when I wear it.
Leather jackets and jean jackets. They look cool but not on me.
I'm a huge fan of leather, denim, and canvas jackets. Of the three, I think it's easiest to find a leather jacket that works because there is so much variety in cuts and colors. The struggle with leather is that it does require a bit of care to keep in good shape, not a ton mind you, but enough that if the jacket is neglected it'll show. Denim and canvas are quite a bit more difficult for people to find something that works for them, as there's a lot less variety there. The nice thing about them though, is they can be tossed in the wash without much worry.
Denim can be versatile, though! I'm currently more of a "Denim jacket with a hoodie" than a "Denim jacket with a floral print", but I think there's room in my life for both I'd love a good leather jacket, though. I might have to do some investigation!