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As someone who doesn't get the gender feelies at all, dresses and sarongs are cool (as in, good for warm weather). High socks are so amazing that everyone wore them for much of the middle ages (they're warm!). Called hosen wool socks and a tunic was ordinary commoner attire. (And yes, your nethers and janglies were free to the open air underneath. Laundry without machines was too labor intensive for non-nobles to have underwear.)

Makeup is weird, but looking amazing is fun. (My experience with it was on stage, and putting on eyeliner was hard to do without flinching.)

While I can appreciate a cool tool (say tweezers with a magnifying lens attached) tactical stuff painted black doesn't make sense in contrast to stuff painted a bright color that can easily be seen (on the assumption that I'm not in combat hidden in cover), bright pink is fine except when everything else is also bright pink. (A lot of beach dayglo colors are meant to be well offset against the ocean greens and blues).

Now that's on the practical side. Some folks get a HUGE buzz from representing according to their gender identity. Trans folk know this because wearing the stuff they like is [regarded by others as] weird in contrast to the stuff that mom bought them while they were growing up, so they've had cause to actually explore this aspect of themselves.

But there are guys who like to double down on butchness and gals who like getting ready for the night out more than the going out, itself. And then there are dudes who, no matter how masculine they represent, feel inadequate and wussy, which likely informs alpha male rhetoric and the far-right man-o-sphere pundits.