Just to follow up on that a little more (maybe I should make a blog post about this)…
Here are three hypothetical kinds of cultures:
culture #1 (sexist): Man wears a dress. It’s either comedy, because men wearing women’s clothing is degrading to men (because women are considered weak/inferior), or it’s dangerous, because he’ll be seen as unmanly and therefore a possible target of hate/violence.
culture #2 (gender-normative): Man wears a dress. People think, “Huh, that guy is wearing women’s clothing. That’s odd. I guess he’s just a feminine kind of guy.” Not a negative judgment per se, but a very gendered one.
culture #3 (gender-neutral): Man wears a dress. Nobody thinks anything about it, because clothing has no association with gender. Pants and dresses are worn by everyone regardless of gender.
The Guenverse is culture #2. By default, girls are given dolls and taught to sew; boys are given wooden swords and taught to fight. If a boy likes sewing, he’s not necessarily going to be seen as wimpy or be teased/shamed about it, but if he doesn’t fight, he might be thought of as not fulfilling his duties (just as a noblewoman who refuses to have babies would be seen as not fulfilling her duties). The attitude is not that liking things associated with the other gender is bad; just that people are born with a set of gender-assigned social obligations. The pressure to fulfill those obligations is strongest on the people at the very top and the very bottom of the social hierarchy; people in the middle (scholars, priestesses, artisans) have more autonomy.
Someday I would like to write cultures that are more like #3. Sadly, our own is still pretty much #1, and men “cross-dressing” in “women’s” clothing is generally considered hilarious. For myself, I know that I will NEVER write cross-dressing as comedy. It’s not funny to me.
(edit: Another thing you’ll never see/hear in the Guenverse is anyone shaming anyone else by comparing them to women. No drill sergeants motivating soldiers by calling them “ladies;” no one saying that someone throws or punches like a girl. It just doesn’t happen.)