Crossdressing can be a very pleasurable activity for those who practice it but is still taboo in society. An example: it’s probably very difficult – or impossible – for you to go to work wearing feminine attire.

This article will show a balanced alternative between monotonous men’s clothing and controversial women’s clothing. You might practice crossdressing in a different way, perhaps not quite in the way you wish, but in a way that is possible.

Starting with underwear: you can wear a bra and panties under men’s clothing, as long as the pieces are neutral colors and seamless. As a last resort, wearing a sports bra can help. But if you’re still not comfortable wearing panties and a bra, you can choose men’s underwear with prints, lace, or even feminine colors – like pink. In any store, you can find pink men’s underwear. You can also wear pantyhose under men’s clothing.

Regarding outerwear: you can opt for tighter-fitting men’s clothing, such as slim fit with prints, colors, and fabrics closer to mimicking the women’s style. A satin dress shirt matched with tighter printed or plain dress pants. A different suit is also possible.

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You can use accessories such as watches, rings, brooches, etc. You can choose unisex models, even opt for feminine pieces, which are often not much different from men’s.

You can let your hair grow a little longer or wear men’s wigs that are a little longer.

Makeup? There are several types and styles of men’s makeup. Maybe it’s not as fun as putting on lipstick, but what matters is the gesture. The same goes for your nails: apply a base polish – there are some aimed at men. What matters is the gesture. I repeat this phrase to show that crossdressing is not necessarily the result, but a process. And the process can also be very satisfying.

Shoes can also help. Choose masculine-made but in a more feminine style.

Society is a little strange: it tolerates women wearing pants instead of skirts, but it doesn’t tolerate men wearing skirts instead of pants. Women should wear a bra, even if they have very small breasts. Men with gynecomastia or chest fat freely parade around shirtless with their nipples showing through their clothes without any type of judgment from others.

We need to circumvent the judgments of society. “She’ll freak out if she sees you in a dress, feminine makeup, panties, and a bra.” Don’t be fooled by the tips given above: despite everything, it may look strange if you’re wearing tighter, patterned men’s trousers. Some will find wearing a satin dress shirt as not normal. A SO may be horrified by your pink or lace brief, even though it is men’s clothing.

I hope that over time people will become more open and tolerant and that the idea of gender-neutral clothing will become more popular. Ideas like unisex dresses, for example, would be interesting.

– Do you have the courage to go out on the street dressed as a woman?

– Have you ever worn men’s clothing with a fit, fabric or color considered “feminine”?

– Do you like the result or the process more when you dress as a woman?

I’m curious about your answers!

Marie Claire


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Active Member
15 days ago

Dear Marie Claire, Already at the age of five or six I realised I had the mind and soul of a girl and that it had suited me much better if I had been born with a body to match that. However I had no idea of either the concept of being transsexual, as it was called back in the early 1970s, the possibility to transition between genders, or the social stigma attached. At eleven I started secretly wearing my mother’s old skirts and dresses to visualise the girl within, and one way or another I continued crossdressing in the… Read more »

Last edited 15 days ago by Marianne
Ellie Davis
Active Member
15 days ago
Reply to  Marianne

Marianne – thank you so much for sharing this.
Du kommer alltid att ha dessa nio år att värdesätta.
I hope I’ve said that right!
Ellie x

Active Member
15 days ago
Reply to  Ellie Davis

You said that as good as anyone Ellie. Thank you.

Alison Anderson
Active Member
14 days ago

Hi Marie Claire, I take a different approach. I am more often than not “stealth dressed," dressed in women’s clothing that looks close enough to men’s clothing, although if you looked closely you could see the difference. I’m almost always in panties (except for wax days when I have to wear boxer briefs, which you could consider as a microfiber tight fitting boxer panties with an extra pouch in front). I don’t wear a bra unless I’m wearing breast forms (or planning on it later). I’m wearing women’s skinny jeans, and a woman’s almost-androgynous tee shirt. There might be a… Read more »

Active Member
3 days ago

@Alison Anderson Thanks for the summary, Alison. You gave me a couple of ideas.

Catharine Connall
Active Member
14 days ago

No to the first two questions but a definite yes to the third. Thank you for asking and for your advice.

7 days ago

Dear Marie, I have crossed that bridge, going to work enfemme. I did it slowly by gradually adding more and more feminine articles through many years. Pierced ears, eyeliner, mascara, painted nails, neutral tunics with Jeggings, etc. It was often very obvious that I was wearing women’s clothes. Men, of course, were standoffish, but women gave me lots of compliments. I finally came in to work one day fully dressed wearing a white top and orange skirt, white heels. By that time, nobody was surprised at all. Men laughed when I walked up to them and it took them a… Read more »

Melody Musick
4 days ago

Hi Marie Claire. Thank you for the wonderful article on “Neutral Crossdressing”. I typically underdress in a bra and panties as well as wear makeup everyday. I dress androgynously in women’s skinny jeans and/or a top or perhaps a blazer whenever possible. I’ve received a few comments and compliments, mostly from women, who remark about my outfit or how nice of a completion I have. I do have question for you and/or your readers. I would like to occasionally begin wearing a ring that symbolizes my crossdressing. I know there is a blue and pink ring that symbolizes someone being… Read more »

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