Why It’s Totally Okay for Guys to Crossdress — And Why Some People Freak Out About It

Let’s talk about something that still makes a lot of people weirdly uncomfortable: men who crossdress. Whether it’s a guy in eyeliner and a skirt at a music festival or someone going full glam with lashes and heels, some folks just can’t handle it. But honestly? There’s nothing wrong with it. At all.

In fact, there’s a lot of self-expression, freedom, and confidence involved when a guy steps outside the gender “rules” and dresses how he wants. So why do some people act like it’s the end of the world?

So... What Even Is Crossdressing?

Crossdressing is literally just wearing clothes that society says “belong” to another gender. That’s it. A man in a dress is crossdressing. A woman in a suit? Same thing—but people don’t usually care when women do it.

Why? Because masculinity is often seen as strong, and femininity is unfairly seen as weak. So when women wear “masculine” clothes, it’s viewed as empowering. But when a man wears something feminine? Suddenly it’s a scandal. That double standard is part of the problem.

Newsflash: Clothes Don’t Have a Gender

Let’s break it down. Fabric doesn’t care what gender you are. Lace, denim, cotton, leather—none of it is gendered. We made all that up.

Go back far enough in history, and you’ll see men rocking robes, wigs, makeup, heels—you name it. From ancient Rome to 1700s France, to traditional clothing in other cultures, gendered fashion is just a social rule that changes over time. So when a guy wears a dress now? He’s just expressing himself. He’s not breaking nature. He’s just bending a few outdated fashion norms.

Why Do Some Men Crossdress?

People crossdress for a bunch of different reasons. And spoiler alert: it’s not always about gender identity or sexuality. Here are a few common reasons:

• Self-expression: Some guys just want to show a different side of themselves.
• Performance: Think drag, theater, or cosplay—it’s creative and fun.
• Comfort or confidence: Sometimes you just feel better in softer fabrics or bolder styles.
• Exploration: For some, it’s tied to self-discovery or even sensuality.
• Challenging gender rules: Why should clothing be limited by gender?

There’s no single reason—and you don’t need one. If it feels good, and it’s not hurting anyone, that’s reason enough.

But Why Do People Get So Mad About It?

Let’s be real: some people straight-up lose it when they see a guy in a skirt. But their reaction says more about them than it does about the guy wearing it. Here’s why some folks get weird about crossdressing:

1. It Messes With Gender Norms

For generations, men have been told to be tough, stoic, and "manly." So when a guy embraces anything considered “feminine,” it throws people off. They feel like he’s breaking some kind of man-code. Which... he is. But that code was dumb anyway.

2. People Fear What They Don’t Understand

If you’ve never seen something before, it might feel “weird.” That’s normal. But instead of asking questions or learning, some people just go straight to judgment. That’s not a crossdresser’s problem—that’s a lack of curiosity.

3. Internalized Misogyny & Homophobia

Let’s call it what it is. A lot of the hate comes from people who still think femininity = weakness, or who are uncomfortable with anything that might blur lines around gender or sexuality. If a guy wears lipstick and it makes someone else mad? That person’s probably got some stuff they haven’t worked through yet.

4. Religious or Cultural Beliefs

Some people were raised in environments where crossdressing is seen as sinful, immoral, or unnatural. But those beliefs come from old traditions—not facts. And we’ve updated a lot of other traditions, haven’t we?

5. Shame and Projection

Sometimes the loudest haters are secretly curious or confused themselves. Instead of dealing with those feelings, they project anger onto others. Classic deflection move.

Let People Wear What They Want

At the end of the day, shaming someone for what they wear just creates more fear and insecurity—for everyone. When we tell men they can’t wear certain colors or styles, we’re reinforcing a boring and toxic idea of what masculinity has to be. And who actually wants that?

Let’s make room for a world where everyone—men included—can express themselves however they want. Life’s more interesting that way. Plus, fashion is fun. We should all get to play with it.

The Bottom Line

Men who crossdress aren’t weird or broken or trying to get attention. They’re just being real. And honestly, it takes guts to be that real in a society that still tries to shove people into boxes.

You don’t have to understand it completely. But you do have to respect it. Because being yourself—whether that means sneakers or stilettos—is something we should all have the freedom to do.