Why I like men who dress as women, and women who dress like men.

‘I’m not ashamed to dress “like a woman” because I don’t think it’s shameful to be a woman.’ – Iggy Pop

Women Iggy

So there’s reason #1: men who dress as women don’t hate women. They just don’t.

Aesthetically it’s fun. It trips up your expectations of beauty, it makes you question what you find beautiful about a man, about a woman. It trips up your notions of what a man or a woman is, where the lines are drawn (hint: there aren’t any. If there are, you’re exploring a map, not a country).

Cross-dressing requires a lot of courage, because women are second-rate citizens, and anyone who may deviate from the “normal” hetero sex model is also a second-rate citizen. A man who chooses to dress as a woman – even in a small way – will provoke a special layer of hatred in some men, and some women. Likewise a woman who is uppity enough to dress or behave like a man receives a particularly bitter type of abuse. You don’t get any chicken-hearted transvestites or genderfuckers. Those guys and gals know how to handle themselves, whether that’s a sharp tongue or a smack in the mouth. If you want to break them, you’d better have brought a tank.


anyone who lives on the fringe, who isn’t dead centre “normal” and who has suffered the slings and arrows of outraged Daily Mail readers, often develops a layer of humour and self-knowledge which is generous, which is not precious or defensive, which is comfortable with itself, not delicate… not about putting people down. There’s an acceptance of self and therefore an acceptance of other people’s weirdnesses.

As a weird creature, I need that open heart like roast turkey needs gravy.


what IS “sexy”? Is it the shape of someone’s body? Or what they’re wearing? For me, it’s the knowledge that inside someone is a cathedral of variety, creativity, depth, myths, a sense of theatre and fun, and that gives me licence to be all that I am with that person. Not just how I look or sound or seem, but all the other stuff (and there is a lot of me). I don’t necessarily mean cross dressing. I’m as happy for you to be a bird comma aves, as a bird comma at a bus stop. Let’s not limit ourselves, here.


because I like my genders and sex roles bent. I like them blurred, smudgy, ill-defined, transgressional, subversive, iconoclastic, idiosyncratic, provocative, a little bit “fuck you”, a little bit “come on in and try it”, playful, confident, expansive. The first thing people notice about me when they meet me is how very female I am. And I’m not. It squashes me into a role I’m not suited to. I’m a gender bender trapped in a very female shaped body. I wouldn’t be one iota different as a person if I’d been born with a cock.

What’s really fun about that is that most straight guys who know me well kind of dig that about me, and kind of dig how it affects them, because it’s very freeing.

So let me share a few beautiful men and one beautiful woman with you:

Women Jude Law
Women John Leguizamo
^ Jude Law, John Leguizamo, both utterly stunning.

Women Rufus Sewell

^ Rufus Sewell – I mean, seriously, LOOK.

Women Heather Cassils

^ OMGOMGOMG Heather Cassils.
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8 Responses to Why I like men who dress as women, and women who dress like men.

  1. Fles says:

    “A map not a country” – I like that a lot.

    You’re absolutely right, of course: people should only ever be regarded for who they are, not what they are or what (or who) they’re doing – and never judged, even then. More: sexuality must never be rigidly defined (although, obviously, some rigidity can be helpful…) – sex isn’t about gender, it’s about a person, maybe a feeling, sometimes just a moment.

    • chiller says:

      Exactly, yes. I have never slept with anyone based on what genitals they happen to have. The spark comes from something else – from who someone is, and what’s in their head and heart.

      Although I’m not going to pretend beauty isn’t a factor, but there are a zillion different kinds of physical beauty.

  2. Daisy says:

    I was going to write something worthy (because it was a truly wonderful piece), but instead I’m opting for pithy:

    OMGOMGOMGOMG RUFUS SEWELL in *that* outfit!

  3. It was an absolute privilege to read. As a man who has an infinite amount of respect for women, and not to mention an aspiring drag queen. I really did enjoy this. I think what is sexy is confidence and humour. Cross-dressing does require courage, but also an element of “don’t give a fuckery”.
    Regardless, this was as always brilliant. And I had NO idea Jude Law looked so stunning as a woman. x

    • chiller says:

      Thank you!

      What’s funny about the Jude Law thing is … I watched the film that still is from because it contained Jude Law in drag. And he was SO good, that about halfway through the film I sort of shook my head and went “JESUS CHRIST THAT IS JUDE LAW!” He totally pwned that role.

  4. Martin says:

    I found your blog just by accident. I was trying to find some pictures of Iggy Pop and I found that beautiful picture of him dressed as women with that article of your full of “deep messages”. I love it, but I would like to know who is chiller? I didnt find any information about you. thanks, Martin

    • chiller says:

      I’m not sure what to tell you! Suspect you can tell more about me from reading the blog than you can from me telling you my shoe size and what my favourite food is, but am in no way averse to answering reasonable questions, if you have any?

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