Here’s a photo from the 1950s, taken at a gathering… Depending upon body type and expertise, some are more successful than others. When crossdressers appear on the street however - when away from support group meetings and drag clubs, they almost always do their best to pass. Here’s a cover treatment by Margaux Schaefer which I was unable to get approved when I was the editor of Tapestry.

In private, at community events, and when making political statements, crossdressers can be as outrageous as they like. Photos like this one from an early 1960s issue of Transvestia, were once common in community publications: Even those not particularly inclined toward fetishism tend to wear clothing women rarely or never wear– I think to a large extent because it takes extreme clothing and makeup on male bodies to produce the images of femininity they desire.

Many and perhaps most crossdressers dress only in their homes or in hotel rooms, where they can indulge their fantasies without fear. Mandycduk1 says of the following Flickr photo, “No point having a maid who is afraid to be seen in public.” More power to her.Ĭrossdresser art takes the imaginations of crossdressers to the extreme, as in this pencil sketch by illustrator Vicky West, which was destined for Summer School for Sissies:

Some crossdressers take their fetishism into public. Why? Because their public appearances aren’t tied to their ordinary lives and to the extent they dare, they can live out their fantasies without affecting their male personas. I doubt that’s true, but crossdressers are more free than transsexuals to dress in stylized or fetishistic ways in public. Crossdressers, it has often been claimed, tend to dress like their mothers.

Mature crossdressers flickr