A Generation Apart

Crossdressers of my generation often have a very different relationship with dressing than millennials and the generations that followed us.

Baby boomers and those who came before us, grew up when the rules were unmistakable. Boys wore boys’ clothes, girls wore girls’ clothes, and anyone who crossed that line risked ridicule, punishment or worse. A boy interested in dresses, makeup or high heels quickly learned that such interests had to be hidden.

So we hid.

Many of us accumulated secret wardrobes, dressed only when nobody was home and became experts at covering our tracks. We invented excuses for buying women’s clothing and worried constantly about being discovered. Even when dressing brought us enormous happiness, it was often accompanied by guilt, fear and the nagging question, “What is wrong with me?”

Eventually, the word “crossdresser” gave many of us a useful identity. It told us that we were not alone and helped distinguish what we did from our sexual orientation or a desire to transition. Support groups, newsletters, conventions and later, the Internet allowed us to meet others like ourselves.

For many older crossdressers, presenting convincingly as a woman became the goal. We practiced walking, talking, applying makeup and coordinating outfits. Passing was not merely an accomplishment; it could also be protection. If the civilians saw us as women, we could go about our business without unwanted attention.

That background may also explain why many boomer crossdressers favor a very traditional presentation. Dresses, skirts, hosiery, heels, jewelry and carefully applied makeup represent the femininity we admired while growing up and were forbidden to experience.

Millennials entered a different world.

They grew up with looser dress codes, greater LGBTQ+ visibility and a much broader understanding of gender. Many younger people do not believe that clothing should be divided strictly between male and female. A young man might wear a skirt, makeup or nail polish without considering himself a crossdresser at all.

Instead, younger people may identify as genderfluid, gender-nonconforming, nonbinary or queer. Some do not bother with a label. They simply wear what they like.

This can create an interesting generational divide.

An older crossdresser may spend hours trying to pass as a woman, while a younger person may wonder why passing is necessary. The older person may enjoy a complete transformation from male mode to female mode. The younger person may combine masculine and feminine elements in the same outfit without feeling any need to become one or the other.

Neither approach is wrong. They simply reflect different experiences.

We boomers learned that crossing the gender line was dangerous, so we tried to cross it as carefully and convincingly as possible. Younger generations are more likely to question why that line exists in the first place.

Of course, these are broad generalizations. Some boomers have enthusiastically embraced newer ideas about gender, while some millennials love nothing more than getting completely dolled up in a dress and heels. Younger people also continue to face rejection, discrimination and genuine concerns about personal safety.

Still, the central difference may be the question each generation learned to ask.

Older generations often asked, “What is wrong with me?”

Later generations are more likely to ask, “What feels right for me?”

That change did not happen by accident. Earlier crossdressers ventured out, organized support groups, shared their stories and gradually became visible. By leaving our closets, we helped make the world a little safer for those who followed.

Now younger generations are taking the next step. They are questioning whether clothing needs a gender and whether anyone should have to enter a closet in the first place.

Wearing Frame

Womanless beauty pageant contestant at Glen Oaks High School, Baton Rouge, Louisiana