DARE TO ASK: Judging men who dress as women

By PHILLIP MILANO, The Times-Union

Question

Why do people associate men dressing as women with homosexuality, but not vice versa? Women can wear men's clothing and nothing is thought of it, but when a man does the same with female clothing, he is stereotyped as gay or not right.

Jim W., Saginaw, Mich.

Replies

In my school, there are a lot of boys wearing girls' clothing. Mostly it's skaters or punks. I wear girl pants and find nothing wrong with it. A lot of my friends do, too. We think they're sweet. Some people have asked me, "Why do you wear those pants; are you gay?" I am straight and so are all my friends.

Logan, 15, Orange Park

A woman in jeans and a collared shirt is not going to stand out like a guy in a dress.

Kelli C., Brandon

Why would anyone want to wear women's clothing? It's uncomfortable, forcibly contorting your body (high heels) or squeezing you so tight you can barely breathe (nylons, bras). And don't get me started on skirts. Men's clothing tends to be more comfortable. The only reason I think women wear women's clothing is that they're expected to and it attracts men.

Avalikia, 22, female, Provo, Utah

What many people forget with fashion history is that tight pants, high heels and the color pink all once belonged to men. And women were historically covered up from neck to heel, while men were the source for physical flamboyance. But the root of this "gay" association is that a woman who chooses masculine things is pursuing the "ideal," and a man who chooses feminine things is going against the ideal. A woman is choosing to be greater, while a man is choosing to be lesser.

Omelio, 24, gay male, Philadelphia

Experts say

We appreciate all the thoughtful replies, which mostly dealt with the cultural ramifications of average folks who occasionally don opposite-sex clothing. Stupid us, however, thought the guy was asking about full-tilt-boogie cross-dressers .

Can we just pretend he was?

Peggy Rudd's been married to one for more than 25 years and has written a number of books on the topic, including My Husband Wears My Clothes (PM Publishers). She says most cross-dressers aren't gay but are just getting in touch with a stronger feminine side than most men possess, one she theorizes probably originated with a greater rush of female-related hormones while they were in the womb.

"These are people who internally are more feminine with their feelings and emotions, but sexually they are men," she said.

Her husband, Mel, got on the phone to confirm that yes, a man in women's clothing is more frowned on than a woman in men's clothing.

"Men think, Why would you belittle yourself to dress like a woman?' Unfortunately many men still see women as the weaker sex ... and many people think if you dress like a man, you are upgrading your position in society."

Phillip Milano, author of I Can't Believe You Asked That! (Perigee), moderates cross-cultural dialogue at Y? The National Forum on People's Differences. Visit www.yforum.com to submit questions and answers, or mail to Phillip Milano, c/o The Florida Times-Union, P.O. Box 1949, Jacksonville, FL 32231. Include contact information.