[JennaHunter]

I’m 47 and growing up it was very frowned on for boys to wear women’s clothes. Especially in small podunk towns. Been married for 18 yrs and my wife isn’t very supportive of me wearing what I want. For the last 6 months or so I’ve decided I want to feel comfortable. With that being said I’ve got a friend that said she’d help me and do my make up so I can go out sometime (drag show). I’m really nervous and have no clue on what to wear. I’m 5’9” 180 no hair and completely shaved. Any help with ideas that won’t make me look like a clown or just a guy wearing girls clothes would be appreciated very much. Thank you for reading this far.

[HelloDiDi]

You want to go out dressed up but you don't want to look androgynous? Its kinda difficult if you look very obviously like average guy. I could say a lot about the absolute stupidity of gendering clothes like skirts which should be totally unisex and allowed for men too outside of kilts... There's something to keep in mind with this, way more androgynous clothing is allowed to certain subcultures and doesn't look off that much. 

Mainly old school punks and goths, at least in Finland if you're a punk or a goth, you can totally go wild and wear really feminine stuff and it wont stand out. Like for a goth guy, corset and a skirt or even certain kind of dress isn't weird. Or very tall boots and skinny fit stuff. Also, goth aesthetic has a whole lot of cartoonish horror feel to it and its the soopky season, Samhain coming up, so why not use that idea? Same with punks, as a part of the rebellious ideas of walking your own path and giving no fucks about make believe authorities, that gives a free pass to break gender norms with clothing too. Also 80's style glam hairmetal stuff could work spot on.

Btw, Ages ago when I presented as a guy back in 2004 I went out once as a goth chick and I loved it, it was also quite passable quite easily and all I had going was clothes and makeup, not even breastforms or anything like that. And people who clocked me were mostly absolutely cool about it, mostly intrigued and curious.

[Stevenator_]

I would 100% wear a skirt everywhere I went if people who live around me here wouldn't absolutely shit bricks.

Check out r/crossdressing on Reddit for some ideas & inspiration. Best of Luck to you.

[tomi66]

I love your candor DiDi, kepp telling it like it is, I too wish people weren't so judgemental

I am with stevenator, would wear skirts all summer long if it didn't make me stand out. It's not that my wife isn't supportive, she's worried about my safety living in such a rural and conservative area, so I just wear women's clothes at home.

I have been traveling for work and have gone out everyday dressed up and it is kind of nice except for the wig. I like the art of putting on makeup and if I still had long hair I would be womanly looking, it helps having breasts and the BO has made mybutt a little more feminine.



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[HelloDiDi]

Thanks. If I could choose, gendering clothes would just stop and everybody could wear what ever they wish without judgement... But then again, brave ones who don't give af about what people think do it anyway. I know a guy in my town who's a known crossdresser and lover gender bending with his looks. He might even be a closeted trans woman, I wouldn't be surprised. 

Anyway, his style is old school hippy/rock n roll thing and he's been wearing female clothes for decades, at least from 80's and on. Also he does makeup and crazy colours which jump out and he just does it and he's one tough son of a gun if some idiot tries to pick a fight or piss him off about it, the guy is just tough as nails and doesn't care. I'm sure he has endured many beatings for it as he has done it since his twenties at least? He's +65 at the moment and still sports femme clothing, makeup and all colours you can imagine.

So how to dress feminine and not get in trouble for it, withstand the abuse, be a part of certain subculture which allows more freedom, or become cis passable one way or another, those are pretty much the realistic options. And then of course going androgynous which is difficult to pull off.

[JennaHunter]

Update, couldn’t go out for Halloween. But I did go buy 3 pairs of cute jeans (bootcut of course) and a pair of women bootie shoes. Just go in 10 pairs of undies. Feeling so comfortable, was nervous about the shoes for a few days. But no one said any bad, just positivity like “I like your shoes”. Feeling a lot better about myself. Thank you all for the encouragement. ???

[Carlana]

I haven't started HRT yet, but I've been going out as a woman, and it's glorious. But I live in a big city, so maybe people are more accepting here. The main things for me are to wear makeup to cover my beard shadow and a wig. My look so far is mostly Goodwill dresses with tights and a sweater. Maybe I'll wear pants like an actual 21 century woman after I medically transition, lol.

[tomi66]

I went out last night when I was in a bigger city and people seem so kind, I am called mam or miss, cars stop when I cross an intersection, men hold doorsand letme go first, it's kind of nice

[robyn]

I wear womens jeans on the weekends and panties everyday

[tomi66]

Always wear panties, I think I have some boxers somewhere.

Short shorts, bra ant tee around the house.