Nice article, I enjoyed the history lesson.
I happen to fit several criteria that stereotype me so I'm not afraid in the least to wear my very favorite hat in public. I wear a black felt wool fedora made by a company called Country Gentlemen. I am a glasses-wearing, fedora sporting, nerdy-looking, atheist, equal rights activist (men, women and everyone else), who dabbles in Libertarian ideas. So I'm pretty much doomed from a stereotype perspective. And I couldn't give a damn less.
If someone wants to judge me by the hat on my head, then they are being foolish. I've lost nothing if someone decides my voice is less important than my hat in judging my character because I am not likely to find common ground with that person anyway. Or at least not enough to form a meaningful relationship.
I also like cuff links, ties, watches, pocket squares, colorful scarves and fancy shoes. In fact, one could argue, if they bought into such ideas, that my love of fashion is feminine. I don't just like men's fashion, I like women's fashion too. I get excited helping out my female friends, my fiance, my sister or mother pick out clothing for themselves. But should someone doubt my heterosexuality because of this love of clothes, again, I don't give a damn. I am straight, but even if someone were to assume I was gay I wouldn't find it an insult. I would think it was kind of silly to equate my hobbies with my sexual preference, but since being homosexual isn't a bad thing, I've no reason to be insulted if someone thinks I am gay.
I also wish makeup was a widely accepted stylistic choice for men. And I don't just mean concealer or blush either. I would love to see people dress in fancy clothes and paint their faces or nails to match. It's body art, and unlike tattoos, a bad choice might only last five minutes.
In short, judging people by how they choose to dress themselves can be just as foolish or idiotic as judging them on any other trait of little significance. Anyone engaging in such behavior should reassess what's important about their fellow human.