How I feel about such statements really depends on the subtext. Context and very subtle differences in sentence structure can project a completely different meaning and intention.
I haven't checked when and in what context your examples (quotes) were said or written, so I can't really comment on them. I do know how I would feel and understand similar statements in different contexts/subtexts, though.
If I felt that someone was trying to order me around, my response would be "How I dress doesn't concern you."
If I felt someone was just expressing what sort of look and style they find more pleasing, I wouldn't be offended, because everyone has a right to express their own opinion and taste, just as I have a right to disagree with them.
If it was said in a context of "It's OK to wear more feminine-looking silhouettes and fabrics to work, if that's what you like," it could even be considered as a positive and inclusive statement.
In general I think a neutrally expressed "dress like a woman" or "dress like a man" phrases are just very dumbed down versions of "feminine look" and "masculine look". When said in a neutral way, I understand them more as descriptors of a certain look and style of dress, than anything regarding a gender (like gender roles, gender expectations, gender identity, etc.).
On the other hand "Think like a man." just sounds stupid. I know some men sometimes use it instead of "Be rational.", but they really don't sound that smart when they say it.
