Hikaro_rin
So, first post outside the welcome. I'm having a heck of a time finding good answers on the interwebs and I see no discussions on the matter here so:
As a closeted bio male, searching to push certain limits, I have two questions.
1. What kind of clothing (male or female labelled) would help a bio male look more androgynous without crossing the line? This is mostly for when I am in my "resting" state between genders.
2. As my social skills are quite weak... If a bio-male were to wear female clothes, say jeans or button up shirts, that resemble male branded clothes how likely would someone be to notice the difference? Are there any particular features (besides the obvious frills and sparkles) that said person should be wary of?
As an FtM with a passion for fashion -insertBratzjokehere- perhaps I can be of service?
I look to visual kei, boystyle (the male counterpart of lolita) and goth fashion for a good example of androgynous clothing. These styles manage to achieve a combination of both male and female wardrobe without an abundance of glitter and rhinestones (although ruffles may be a factor, but who could possibly say no to ruffles?). The key, I feel, is to not focus on the clothing itself but the overall look.
To begin building an androgynous wardrobe, I would start collecting bracelets, necklaces and perhaps some stud earrings. Males
can wear studs and necklaces and get away with it. This would also help you achieve androgyny with the above-mentioned jeans and button-down shirt. The only difference between a male button-down and a female button-down is the side on which the buttons are sewn, so you should be good. As for jeans, if they're flared or skinny or have any embroidery on the back, people will easily be able to tell the difference. It largely depends on your body type as well, especially if they're basic boot-cut.
Colors are also a thing you'll want to pay attention to. Go for bright and boom, and shy away from drab shades and pastels. Nobody likes wearing pastels. Black is the only exception to the drab ban, because it's classy, basic, and looks great with everything. Colored jeans, white jeans and jeans with a pattern are also things I've seen males wear to get to a more androgynous middle line.
Finally, hair and cosmetics are a thing I would recommend playing with. A sassy side cut helps a lot with androgyny, as does a touch of eyeliner or mascara. Also check out some hairstyles and ways of using cosmetics, both male and female, from Asian pop culture and see what you like.
In the end, don't shy away -at all- from dressing up. Back when I was still attending college, I dressed to the nines every day in whatever style I was feeling. Sure, I got funny looks, but I felt good and I knew I looked good. Classy men dress up just about as much as classy ladies, and the more often you dress up, the more your androgyny/fluidity will be perceived and respected by those around you.