by Jenn der Bentson

Crossdressing has existed for as long as fashion has had gender rules—but even today, it’s still something many people keep hidden in the closet. Whether it’s fear of judgment, misunderstanding, or losing the respect of loved ones, countless crossdressers—especially men—feel they must keep this part of themselves secret. But what if we could change that?

What if we lived in a world where expressing gender through clothing wasn’t met with shame, but curiosity? Where a man wearing a dress wasn’t shocking, but simply another form of self-expression? The truth is, we need more open and honest conversations about crossdressing—not just within the community, but in society at large. These conversations have the power to dismantle shame, build bridges, and help people live fuller, more authentic lives.

The Silence Surrounding Crossdressing

Let’s be real: for many men, the desire to crossdress doesn’t go away. It’s not “just a phase” or a quirky impulse. For some, it’s about exploring femininity, comfort, or sensuality. For others, it’s a deep part of their identity. But because crossdressing defies traditional ideas about masculinity, it’s often viewed through a lens of suspicion or ridicule.

Most people simply don’t understand it. And when something is misunderstood, it often becomes taboo. That taboo turns into silence—and that silence breeds shame.

When someone can’t talk openly about something so personal and meaningful, it creates an emotional prison. People feel alone. They doubt themselves. They might wonder, “Am I broken? Am I weird?” But here’s the truth: you are not broken. You are not weird. You are human.

And you’re not alone.

Why Open Conversations Matter

So why should we be talking more about crossdressing?

Because silence reinforces stigma. When we don’t talk about crossdressing, it allows outdated stereotypes and harmful assumptions to fester unchallenged. But when we start having open, honest conversations, we begin to replace those assumptions with understanding.

Conversations educate. They normalize. They offer connection. They also help people outside the crossdressing community see the person behind the pantyhose or the lipstick—not a “man in a dress,” but a complex, kind, creative individual expressing themselves in a way that feels true.

Imagine how different things would be if more people knew that crossdressers are fathers, husbands, partners, professionals, and friends. That many of us live full, healthy, loving lives—just with a wardrobe that expands beyond societal expectations.

Open dialogue also helps the people closest to us—partners, family, friends—understand what crossdressing really is (and what it isn’t). It’s not necessarily about wanting to transition. It’s not always sexual. It’s not a betrayal of one’s masculinity or a relationship. But without these conversations, misunderstandings grow, and they can damage relationships unnecessarily.

Breaking the Myth of Masculinity

At the root of society’s discomfort with male crossdressing is a toxic idea: that men must always be strong, stoic, and “masculine” in a very narrow sense. In this rigid box, wearing something feminine is seen as a weakness or a threat to one’s manhood.

But what if true strength lies in authenticity? What if masculinity could include softness, elegance, vulnerability, and beauty?

The desire to crossdress challenges the outdated script of what it means to be a man—and that’s a good thing. We don’t need more people locked into roles they didn’t choose. We need more freedom to express ourselves honestly.

The more we talk about crossdressing, the more we chip away at that old myth. We open the door to a healthier, more inclusive understanding of gender and expression—for everyone.

Creating Safe Spaces—Online and Offline

For many of us, the internet was the first place we could really be ourselves. Message boards, Reddit threads, YouTube channels, and blogs became lifelines—proof that we weren’t alone, that others felt the same tug of identity and expression.

These online spaces remain vital. But the next step is bringing those conversations into the physical world. That doesn’t mean everyone needs to come out publicly or wear heels to work (unless you want to!). It means gradually building a culture where curiosity replaces judgment.

Whether it’s confiding in a partner, showing a trusted friend a photo, or attending a meetup, every honest conversation plants a seed. Over time, those seeds grow into understanding—and that understanding changes lives.

It also helps when allies speak up. When people who don’t crossdress themselves support those who do, it sends a powerful message: that self-expression is not only okay—it’s something to be celebrated.

How to Start the Conversation

Talking about crossdressing can feel scary. But it can also be liberating. Here are a few tips to help open that dialogue—whether you’re speaking to a partner, a friend, or someone new:

1. Be honest, but patient. Not everyone will understand right away, and that’s okay. Give them time to absorb what you’re sharing. 
2. Share your story. Explain what crossdressing means to you personally. Is it emotional? Aesthetic? Spiritual? Everyone’s reasons are different—and your story is valid. 
3. Be open to questions. When someone asks out of genuine curiosity, that’s a chance to build a bridge. 
4. Don’t let shame drive the conversation. This is part of who you are—it’s not something to apologize for. 
5. Know your boundaries. You don’t owe anyone your full story. Share what feels right for you.

And for those who are still waiting for the right moment to speak—know this: your silence doesn’t make you any less valid. But if and when you’re ready, know that your voice matters.

Looking Ahead

We’re living in a time when more and more people are questioning old ideas about gender, identity, and expression. That’s progress—and crossdressers have a role to play in that cultural evolution.

But change doesn’t happen in silence. It happens through stories. Through courage. Through community. By talking about crossdressing openly, we make it easier for the next generation to grow up without shame. We make space for more honest relationships, deeper self-acceptance, and a more compassionate world.

So let’s talk about it. Let’s tell our stories. Let’s ask questions, give answers, and support each other.

The world needs your voice—just as much as it needs your style.