Sure you can dress to the nines in your new cocktail dress to attend parties hosted by your fellow transpeople, but attending holiday gatherings hosted by civilians, that is, non-trans family and friends, usually means dressing in boring boy mode.
But dressing like a boy does not have to be humdrum if you are willing to push the envelope. You can feminize your boy look just enough to please your inner girl, while maintaining enough boyishness so that civilians won't question your gender.
Dressing like the fellow pictured to the right would allow you to do just that.
His hairdo is decidedly male, but was highlighted by his hairdresser to femme up his crowning glory. He wears minimum makeup --- just foundation, tinted lip gloss, mascara, eyeliner and eyeshadow, which allows him to look pretty, but still maintain a boyish appearance.
His black crepe romper with the silk satin bow tie hints at his feminine side, but still maintains a semblance of masculinity --- after all, he is wearing pants, not a dress. Jumpers and rompers often have no pockets, so he has a perfect excuse for carrying a man-clutch (he has to store his money, keys, hankies and makeup somewhere).
Mantyhose were optional, but depilation was not; no boy would be caught dead with hairy legs in an outfit like this, so a close shave of his manly gams was in order. To complete the look, flats would be a bust --- a pair of sexy man-heels were a must.
Finally, our fashionable fellow added the colorful necklace to make a feminine statement in case anyone missed the other feminine clues.
This ensemble might be too edgy for some of us. Uncle Billy and Ma Bailey might faint dead away at the sight of a male relative showing up for Christmas Eve dinner in this outfit, but on the other hand, it may be acceptable in more diverse family settings. Your mileage will vary.
If this outfit is too over the top for you, you can push the envelope without breaking it like I did today.
It is the last day of work here before the long weekend shutdown. Many of my co-workers are already taking time off. I estimate that we are about half staffed today, so it is a good day to push the envelope a bit; with fewer co-workers in the building, there are fewer chances for confrontations (not that I expect any, but you never know).
With that in mind, I feminized my look when I dressed for work today.
My underwear consists of black panties, waist cincher, black camisole, and black tights.
Over that, I am wearing my long red tunic sweater that falls to the top of my thighs, black slacks with a side zipper and no pockets, and black patent flats with a silver buckle.
I even wore a little makeup: a light coating of mascara along with my standard pink tinted lip balm.
I considered wearing a bra instead of the camisole, but I thought that C-cups would be too noticeable under the sweater. I also considered wearing a purse, but I had to carry my computer bag, so I was able to store everything I needed in the bag.
I made the rounds through the building twice already and no one has mentioned my outfit, but I feel so womanly that I am glowing.
