My personal philosophy- People, tastes and preferences all differ from person to person. What might be right for you simply might not be for someone else and vice versa. That doesn't make it wrong, in my book; only different. Does one's personal attire accurately reflect the kind of person they are? Maybe yes, maybe no. That said, how would you know unless you got to know that person? Not just that 'type' of person (from a stereotypical perspective) but that specific person?
From my standpoint: I really don't care what someone else has on their wrist, or what shoes or shirt they're wearing or how they look; it's not on my wrist, I'm not forced to buy it and someone else's preference in what possessions they choose to own does me absolutely zero harm. And likewise the other way around. I wear what I enjoy to please me, no one else. If someone wants to tell me what they think of my choices, that's absolutely fine. Everyone is entitled to an opinion. Would it bother me? Not one bit as I'm not out to please others. Bottom line- tastes differ. Variety makes the world go around. Heck, variety is the spice of life, as quoted by your sig. I think there's a lot more to worry about in life than what someone else has or chooses to wear.
Just sayin'...