Endpoint: Gender Fluid

I know a few women who dress androgynously.  I know one born-male who slides back and forth between male and female and seems comfortable on any stops along the road.

I can appreciate people who are comfortable going back and forth, or partially dressing, or wearing makeup with their male clothing daily.  I've played with this a bit.

I've worn clear nail polish, neutral lip gloss, brown mascara, and carried a bag.  I wear jewelry that is clearly women's.  But I only wear "passable" women's clothing when I'm in drab ~ a close look would reveal buttons on the wrong side on a shirt, or that those socks are really tights, or that my dress shoes are a bit more femme than most.

I don't see myself wearing a skirt or lacy top or kitten heels (I have worn Mary Janes with very low heels) when in drab but if that was an activity that was more-or-less ignored by society I might.

I am by no means a fashion leader, but if I can make some small inroads into female clothing allowable for men, I'll try.  But people with a larger audience than me have tried and failed.  "Glam rock" makeup has never gotten wide acceptance, nor has the Seinfeld puffy shirt, nor kilts for general wear.

I would discourage guys from trying to do male one day, female the next at work.  I think employers would see that as disruptive and it would be a disservice to the community.

---