This image says it all, and represents one of the reasons I’m so passionate about supporting men who like to wear what is usually regarded as being ‘women’s clothing’ like lingerie, dresses, skirts, etc. Nobody bats an eye when a woman puts on men’s clothing, in fact, it’s often seen as rather sexy. Case in point, Katherine Hepburn wearing what was regarded as being male attire at the time.

I’ll end this little celebrity celebration of crossdressing with one of my favorite images, Tarantino in high heels. What I most love about this image is the way his lower legs and feet look so feminine but he’s traditionally male on the top. It’s like the mullet of crossdressing.

This is the final part of the series from GR8legs about meeting his anima. This has been a really interesting and insightful series and I’ll be posting it as a complete page soon. My thanks to Gr8legs for his considerable contribution to the site and to readers’ understandings of what it is for one man to wear women’s clothing.

Crossing the Rubicon

Following on from the elation that I‘d felt after trying the waist cincher for size before buying, I once again found myself in the same shopping centre on the Friday. As I wandered around, I found myself being drawn into one particular shop. I had never had the intention, nor did I feel I would ever move into the world of also wearing female outer garments, but as I was browsing in the store I found myself seeking out a skirt and top, as well as a belt to complete the outfit.

That evening my girlfriend came to my house and I dressed in the outfit to show her my new purchases. She loved the outfit and I talked with her about “Ava”. As we were standing outside on the patio, I walked across to put my empty beer bottle in the rubbish bin. I strode across in a relaxed, confident manner and when I returned to stand beside my girlfriend, she put her arms around my neck, gave me a big kiss and with a bigger smile told me that she’d never seen me so relaxed & confident in all the time she’s known me. She then said that she likes Ava and that she’s glad I’ve finally made friends with her.
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Because much of the objection to men wearing women’s clothing comes from women, I like to address the feminist issues associated with men wearing women’s clothing from time to time. It might surprise you that there are any feminist issues associated with men wearing dresses and lingerie. After all, isn’t it simply a men’s issue?

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This is a two part post about the state of feminine fashion when it comes to men, and the reasons behind it. If you were looking for a reason to wear a dress, you’ll find it here.

What do you think when you hear the words, feminine fashion? Do you imagine skimpy skirts and tube tops? Do you imagine pretty lacy undergarments? Do you imagine long floral dresses? Do you imagine short shorts and a tank top? Perhaps you imagine jodhpurs and a riding jacket, or maybe a sharp two piece business suit?

Read… A Man In A Dress | All Fashion Is Feminine

Men must wear dresses. In fact, I would like to posit the theory that until all men are able to walk about in dresses without fear of mockery, losing their jobs or putting off potential mates, we will not have achieved freedom and equality in our societies.

Read… Why Men Must Wear Dresses

When thinking about lingerie, it is important to think outside the box. You see, many of us get caught up in notions handed to us at birth, notions like the fact that the sky is blue, grass is green, girls wear panties and boys are left with whatever scraps of cotton are left over.

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If you happen to be a guy who at some point developed a fascination with women’s clothing, you’ve probably spent a good deal of your life since that time feeling guilty and disliking yourself. I don’t say that because I’m some guru with a deep insight human nature, but because I’m a human with eyes, and any human with eyes can see that if there’s anything that modern living sets us up for, its feeling guilty and giving us reasons for disliking ourselves.

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It is surely no secret by now that many women aren’t exactly on board with the men in their lives wearing women’s clothing. We can point out at great length how much of a double standard this is (I wonder how many women have been wearing jeans whilst they complained that the man in their lives wanted to wear a skirt or lingerie) but the type of woman who is put off by a man who wears women’s clothing doesn’t care about logic of that nature.

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Let me cut to the chase on this one real quick. No. Especially not if you’re a woman, but also even if you’re a man. At least, to my mind at least, the act of simply wearing clothing designed for women does not make a man a cross dresser. Some men wear skirts and lingerie and other items of women’s clothing for no other reason than the fact that they like them. They are not trying to be feminine, they are not trying to pass as women, they are simply men going about their day in skirts or lingerie or whatever pleases them.

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Since I have begun exploring the themes of gender and dress, I’ve occasionally received feedback from readers who are disappointed at the breadth of the issues these articles cover. ‘I thought this was just for men who liked lingerie’ is the most common of their refrains.

Men who fall into this category get their panties in a knot every time issues like wearing women’s outerwear or gender neutral people arise.

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Are you male or female? You no longer have to be either, at least in New South Wales Australia, where local government has taken a great leap forward in allowing the option of no gender to be assigned on birth certificates. This allows people born without clear gender, those who ally themselves with neither the masculine or feminine to live as they wish to, neutrally.

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One of the hardest things for men who like feminine clothing is the fact that they often have manly traits that make the feminine clothing seem, well, unfeminine. In particular, an abundance of body hair often gets in the way, cluttering up the place and creating a clash of the worlds that some men find problematic.

The best solution, in my limited opinion, is to simply embrace the contrast. There’s nothing like a lovely handlebar mustache above a sweet pink nylon nightgown.

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I told you I’d return to this issue, and so I have. Here’s a bit of a breakdown about race, gender issues and men who wear dresses for personal fulfillment or alternatively, to be laughed at.

This article came to be after I watched a video clip of Dave Chapelle talking about a time he refused to wear a dress in a movie. He went on to explain that he felt that Hollywood always tried to put strong black men in dresses for amusement value and that it was, on some level, degrading to black men. “They put every black man in the movies in a dress at some point in his career,” Chapelle says.

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