I have always dressed a bit unusually. Conservative (I think, although nothing like the LSE's) but distinctive. I actually have two shirts like the one Pitbull is wearing. They are identical and one of my favorites, and they go well with a business suit I wear. I button the shirt up higher, though.
No pastel pants. Otherwise, white shirts, blue shirts, gray wool pants, black belt, black leather shoes. I stopped wearing a watch, but when I did, it was a square, thin gold watch with a white face, minute and hour hands, twelve marks for hours, burgundy alligator strap.
When I was at the U of M, I wore some pretty colorful shirts with shoulder-length hair. I had a ponytail for a while. My father, who was in the military, hated the look, but I was just being honest about who I was.
Regarding dressing unusually for my gender, I don't think I do. Maybe I'm a bit out there. A guy at work said he thinks I dress pretty well. I like to be ready to meet customers or vendors 100% of the time. But I have noticed that, after I got divorced and removed my wedding ring, I did start getting some speculative looks from some male waiters and barristas. I've also gotten some wary looks from guys in the military when they notice I'm not wearing a ring. But I just don't play on that ball team, and apparently, they can tell that after a very few minutes.