RetroProgressive – Scary Halloween fashion

It’s the time of year when people dress up in all sorts of strange costumes for Halloween parties. I was reminded of Nige’s closing comments in a post a while ago when I read about the Washington DC Drag Queen Race. Apparently this is one of the area’s more unique Halloween events: “Each year on the Tuesday before Halloween, thousands of spectators flock to Dupont Circle to watch costumed drag queens show off their elaborate outfits and race down 17th Street. The informal block party lasts a few hours and attracts a diverse crowd”, as can be seen from the photos in this post.

Despite my love of dressing up, the idea of cross-dressing has never really appealed. Not because I’m against that sort of thing. As far as I’m concerned, each to their own so long as it doesn’t offend, and isn’t an unworthy use of tax payers’ money. And, having worked in the fashion industry, I’ve met quite a few transvestite types in my time. Marginalized by their unconventional taste in clothing, they’re a peculiarly secretive and somewhat old fashioned bunch – with the notable exception of the national art treasure and curiosity that is Grayson Perry, of course.

Anyway, recent research has confirmed that most transvestites aren’t homosexual, so they’re genuinely inhibited when it comes to buying women’s clothes. What heterosexual man wouldn’t feel uncomfortable walking into a ladies’ clothes shop and trying on dresses? But now the advent of online shopping has changed all that, and men can buy larger sized shoes and clothing without having to suffer the embarrassment of finding themselves in a communal ladies’ changing room… hem, hem.

One website claims that “Being a modern cross-dresser is a great deal more acceptable in today’s society than ever before and it can be extremely fun and exciting to…really show and express your outer self and alter ego with impressive and realistic results – whether you need a new lipstick, a stylish wig, some sexy boots, silicone breast forms, exotic party dancewear, sissy dress, fancy dress outfits, disco clothes, sexy leather clothing, or kinky costumes.”

But herein lies the problem. A wig is almost always obviously a wig. Jellyfish like silicon bra inserts will never look entirely realistic. Men who cross-dress invariably opt for high-heeled shoes, which they’re not used to walking in, so tend to teeter along the pavement – the sort of impracticality most women go out of their way to avoid. Men dressing as women also want to appear as feminine as possible, and are likely to choose frilly dresses with lace and ribbons, petticoats, corsets, girdles, stockings and suspenders. They insist on wearing false eyelashes and low cut tops – and end up looking like a cross between Dame Edna and Barbara Windsor.

In Wendy Jones’ biography, Grayson Perry: Portrait of the Artist as a Young Girl, Perry says, “I learned that it is rare to meet a transvestite who is convincing; most aren’t credible, they are blokes in dresses with wigs on. The stereotype is a man in his fifties in old-fashioned women’s clothes, perhaps a knife-pleated skirt with tan tights. Trannies are part-timers, they’re amateurs…”

Seeing man-sized bodies squeezed into outmoded women’s fashions can be a decidedly scary sight. Yet, in terms of tranny style, not a lot has changed since the wonderful impersonator Dick Emery’s day…

Even with the benefit of today’s cross-dressing makeover services, men will always be dabblers in the art of female attire. However, the most scary thing isn’t seeing a man dressed up as a woman – it’s when she looks just like a woman, but is in fact a man.

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About Author Profile: Susan Muncey

Trend consultant Susan Muncey, is Editor of Visuology Magazine. In 2008, she founded online curiosity shop, She writes on style and trends for several blogs, including, and The Dabbler. She previously owned cult West London boutique, Fashion Gallery, one of the first concept stores in the world. Susan graduated in geography from Cambridge University and is also an Associate Member of the CFA Institute. She lives in London with her husband.

10 thoughts on “RetroProgressive – Scary Halloween fashion

    Gadjo Dilo
    October 30, 2010 at 08:37

    I once had a friend who was a 6’5″ gay German computer programmer and body-builder. He was also a tranny and quite entertaining with it, as can perhaps be imagined! Excellent chap.

    Gadjo Dilo
    October 30, 2010 at 08:38

    p.s. My, wasn’t Dick Emery good, back in the day.

    October 30, 2010 at 08:48

    Yes, Gadjo – Dick Emery was a brilliantly funny and very versatile chap. I’ve just bought a dvd of one of his old films, where I believe he plays most of the characters.. just need to find time to watch it.

  4. Gaw
    October 30, 2010 at 09:33

    I can see the attraction in wearing a skirt, particularly on a hot day. A nice, light, flouncy one. However, as my reasons are practical I don’t think it betrays much of a transvestite yearning… I can’t see me ever having the courage though. Sometimes, you’ve gotta hand it to Becks.

    October 30, 2010 at 10:10

    Why not a Welsh kilt, Gaw? That wld attract no undue attention (hem hem)…
    Down my way, the trannies make no effort to look like women. I saw one the other day striding around quite unselfconsciously dressed in the style of Doris Day circa 1960 (white pedal pushers, blue cotton blouse etc), all set off with a thick, well-tended beard. Why??

  6. Gaw
    October 30, 2010 at 10:57

    Assuming its existence, the problem with a Welsh kilt (as with a Scots one) is that it would be made of wool. Its heat-retaining properties would defeat the practical attractions of a flouncy skirt. And then there’s the itchiness… The fact that there aren’t cotton kilts seems to me emblematic of the drawbacks of a nativist nationalism. Oh yes.

    October 30, 2010 at 11:34

    Thanks so much for a very enjoyable article. The town here is plastered with ads for a Night of the Dead Celebs fancy dress Halloween party so I guess dressing up is as popular as it was. The local museo has some wonderful Ikat robes from Central Asia and shimmering embroidered silk numbers from ancient China, coats of many colours which must have vanished here with the Elizabethans. I think we’ve paid a heavy price for the old Puritan suit. I’ve always thought the arguments for it – as a leveller – are a little specious.

    Grayson Perry was featured on the radio this morning. He has commissioned a transvestite motorcycle. I’d imagine this must be good for scattering a posse or three of Hell’s Angels.

    October 30, 2010 at 13:51

    Gaw, Jean Paul Gaultier says every fashionable man should have at least one skirt in his wardrobe… Btw I recently saw a group of a group of Scottish Boy Scouts who were queuing to go through security screening at an airport – there are some occasions when kilts aren’t particularly useful. Poor boys, they looked so out of place.

    I also forgot to mention a rather surreal experience I had a few weeks ago. A partially sighted lady was having difficulty finding the make-up in Boots, so I helped to direct her and then offered to help her up the road to another shop. It wasn’t until we got outside that I realized ‘she’ was actually ‘he’. So I had to walk a good few hundred yards with a tranny in high heels holding onto my arm. We had rather a nice chat. And I didn’t let on that I knew her little secret.

    Nige, I’m a fan of Doris Day films, as well as Dick Emery (though haven’t taken to dressing like either yet). Mark – I should visit your local museum, it sounds like a treasure trove of curious clothing. Thanks for the link to Grayson Perry’s motorcycle – it’s so Barbie!

    October 30, 2010 at 14:45

    PS – Nige, as for why? I think we need a psychoanalyst to answer that one. Or just blame it on the parents (responsible for most of life’s curiosities).

    October 31, 2010 at 09:28

    Well my bro and I enjoyed dressing up in our mother’s clothes as much as the next pair of red-blooded lads, but [a] we grew out of it very quickly, and [b] we always knew it was a silly thing to do and we looked ridiculous. I don’t think you could be a tranny – at least of the beard-sporting kind – unless yr sense of the ridiculous was nonexistent.

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