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In my observations, some of the stereotypes seem to be applicable. I have seen that there is a tendency for females in traditionally male positions to be less feminine and more like "one of the guys" and for males in traditionally female roles to be a bit less masculine. This is certainly not a universal trait, just something that I have tended to notice. Two of my case studies at my work are a male secretary and a female construction technician. He is very neat and tidy in his appearence, somewhat fastidious, with a very feminine manner. He is married with children, but he does not come across as a man's man. She dresses like all of her male co-workers. No jewelry, no make up. She carries herself like a man and talks shop like all of her male co-workers. She is married with children.
I think about how Hollywood approaches folks crossing the gender lines, characters like Mrs. Doubtfire and Victor Victoria. Of course these are folks who are pretending to be someone of the opposite sex to fit in and get what they want, and obviously these are humorous caricatures. However, I wonder how much of my "real world" observations of people's demeanor and appearance are based on how they believe they need to act in their roles in order to fit in and be successful. Perhaps some of the choices are conscious, perhaps some are subconscious. Maybe there is some crazy hormonal osmosis at work here. Folks take on the coat that others in their position are wearing. They begin to take on the mantel of the stereotype. What have you observed?