Walk into any major city today and you might see it. Or maybe you see it on TikTok. A guy in a skirt, or maybe a full gown, or just some heavy eyeliner and a silk blouse. It's everywhere now. But here is the thing: a man dressed like a woman isn't some new "woke" invention of the 2020s. Not even close. If you look at the broad sweep of human history, the way men dress has always been a moving target, shifting with the wind of politics, theater, and sheer necessity.
Context is everything.
In the 1600s, it was totally normal for men to wear high heels and silk stockings. King Louis XIV was famous for it. He wanted to show off his legs because he was a dancer. Back then, those weren't "woman clothes." They were "rich people clothes." Fast forward to today, and we’re having a massive cultural conversation about what it means when a man steps outside the traditional "pants and a t-shirt" box. Some call it drag. Some call it gender-fluid fashion. Others call it cross-dressing.
Honestly, the labels are getting a bit messy.
Why the Man Dressed Like a Woman is Such a Big Deal Right Now
Social media changed the game. Before Instagram, if a man wanted to experiment with feminine clothing, he usually did it in private or in specific subcultures like the drag scene or the ballroom culture of 1980s New York. Think Paris Is Burning. That was a community of survival. Today, it’s a mainstream aesthetic choice seen on red carpets.
Take Harry Styles. When he appeared on the cover of Vogue in a Gucci dress, it sparked a month-long internet war. Why? Because for many, the image of a man dressed like a woman challenges a very specific, very rigid idea of masculinity that took hold during the Industrial Revolution. Before that, men were basically peacocks. We’ve spent the last 200 years in what fashion historians call "The Great Masculine Renunciation." This was when men collectively decided to stop wearing bright colors, jewelry, and elaborate fabrics in favor of the drab, utilitarian suit.
We are finally seeing the end of that era.
It’s not just about celebrities, though. You see it in high-fashion houses like Maison Margiela and Thom Browne. Browne has basically built a multi-million dollar business selling pleated skirts to men. And people are buying them. It’s a shift from "costume" to "wardrobe."
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The Difference Between Drag and Daily Life
One big mistake people make is grouping everyone together. A drag queen is a performer. Drag is an art form, usually rooted in exaggeration, camp, and satire. When RuPaul gets into "geish," it’s a job. It’s theater.
But then you have the casual cross-dresser or the gender-nonconforming person. This isn't a performance for them. It’s just how they feel comfortable. Dr. Vern Bullough, a famous historian who studied gender, pointed out that clothes have always been a primary way we signal who we are to the world. If a man feels that "menswear" is a cage, he’s going to look for the exit.
The Psychological and Social Pushback
Let's be real. It’s not all sunshine and rainbows. There is a lot of genuine anger and confusion when people see a man dressed like a woman.
Psychologists often talk about "gender policing." This is the internal urge people have to make sure everyone stays in their assigned lane. When someone deviates, it creates "cognitive dissonance." Basically, your brain short-circuits because it can't quickly categorize the person in front of you. That discomfort often turns into mockery or even violence.
However, the younger generation—Gen Z and Gen Alpha—don't seem to care as much. To them, a skirt is just a piece of fabric with a hole in the middle. They don't see the "moral" weight that older generations do.
From Shakespeare to the Silver Screen
We have to talk about the stage. For centuries, women weren't even allowed to act in England. Every female role in Shakespeare’s plays—Juliet, Lady Macbeth, Rosalind—was originally played by a man dressed like a woman. It was a legal requirement.
Then you have the 20th-century comedy trope. Some Like It Hot, Tootsie, Mrs. Doubtfire. In these movies, a man putting on a dress is the "joke." The humor comes from the supposed absurdity of a man being "degraded" to the status of a woman.
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That’s a heavy concept to chew on.
If we find a man in a dress funny, what does that say about how we value women? This is what feminist scholars like Judith Butler have been arguing for decades. Butler’s theory of "gender performativity" suggests that we are all essentially "in drag" every day. You "do" being a man by putting on the tie and the boots. You "do" being a woman by putting on the heels and the makeup.
Modern Practicality: It’s Just Fabric
Some guys are doing it for purely practical reasons. In 2017, bus drivers in Nantes, France, wore skirts to work because their company wouldn't let them wear shorts during a heatwave. Since women were allowed to wear skirts, the men just used the loophole.
It worked.
The same thing happened with schoolboys in the UK. When the "no shorts" policy hit, they showed up in the official school kilts. It’s a brilliant way to point out the logical fallacies in our dress codes.
Practical Insights for Navigating This Shift
If you’re someone who is interested in exploring feminine fashion, or if you’re just trying to understand the person in your life who is, here are some things to keep in mind.
First, language matters but don't obsess over it. Most people are okay with you asking questions if you're being respectful. "Cross-dresser" is a bit of an older term. "Gender-fluid" or "non-binary" are more common now, but they don't apply to everyone. Some guys are 100% men; they just like the aesthetic of a dress.
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Second, the "rules" of fit are totally different. Menswear is usually boxy. Womenswear is cut for curves. If a man dressed like a woman wants to look "natural," he usually has to look for specific cuts like A-line skirts or empire waists that create the illusion of a different silhouette.
Third, acknowledge the safety aspect. Depending on where you live, walking down the street in a dress as a man can be dangerous. It shouldn't be, but it is. This is why many people start in "safe spaces" like private clubs, certain neighborhoods in big cities, or online communities.
What We Get Wrong About the History
People love to say that "men used to be men." But look at the 18th-century "Macaronis." These were young English men who traveled to Italy and came back wearing massive wigs, tiny hats, and bright, flowery coats. They were mocked for being "effeminate," but they were also the height of fashion.
Fashion is a pendulum. We moved from the ornate 1700s to the boring 1900s, and now the pendulum is swinging back.
Actionable Steps for Understanding or Exploring
If you want to dive deeper into this topic or even try shifting your own style, start here:
- Research the "Great Masculine Renunciation": Understanding why men started wearing boring clothes helps you realize that the current "rules" are only about 200 years old.
- Support Designers Breaking the Mold: Look into brands like Harris Reed or Palomo Spain. They are designing clothes specifically for the male body that use "feminine" elements.
- Separate Performance from Identity: Remember that a man in a dress might be a performer, a trans person, or just a guy who likes the breeze. Don't assume you know their life story based on their hemline.
- Look at Global Cultures: In many parts of the world, men wearing "skirt-like" garments is the norm. The Sarong in Southeast Asia, the Kilt in Scotland, the Thobe in the Middle East. The Western "pants-only" rule is actually the outlier.
The reality is that clothes are just tools. We use them to stay warm, to look good, and to tell the world who we think we are. If a man dressed like a woman feels more like himself, he’s just using a different set of tools. It’s a trend that has happened before, and looking at the current trajectory of fashion, it’s one that is here to stay for the foreseeable future.