I don't understand why people care about this.
Like, you do understand that fashion changes over time, right? High heels used to be considered "masculine", for instance, since heel were more practical when riding horses (and you'll still see them on cowboy boots) but then they started to introduce them to women's fashion they fell out of favor. Mind you, I could totally understand hating fashion; it's always been something created by and for social elite. And you can certainly question what fashion is trying to say; since few things are politically neutral...
Still, I think there's more important things to worry about that the clothes someone wears. I'd rather live next door to a neighbor that wears a skit, but is still a friendly dude who'd help people around him, that a gruff manly man who dresses like a man should - whatever that actually means - but is a dick.
And this is coming from someone who has a "t-shirt and jeans" (nothing more iconic when it comes to American masculinity ) fashion sense.