What wearing a skirt as a man mean
Posted: Fri Aug 22, 2025 3:42 pm
I'm posting an article on skirt wearing
Does wearing a skirt as a man mean I’m gay or trans?
I’ve wanted to write a post about this topic for quite a while because this is one of the first questions that a lot of men ask themselves or are asked when they first discover their love for clothes typically found in the women’s department. I’ve already written about my own experience with fielding that question from my own mother.
When men wear skirts, heels and dresses, there is frequently a societal association with queerness. For years, wearing gender-non-conforming clothing was primarily associated with homosexuality, but in more recent years, transgenderism has also become more prominent in the popular discourse. The US Secretary of Defense, Pete Hegseth, even recently called trans women “dudes in dresses,” thus confirming the association.
Gender-Non-Conformity and Homosexuality
So, why do so many people associate these two? The answer to that lies in the centuries-long tradition of gay men dressing in clothing typically associated with women. For some, it is an essential part of their queer identity. Any event that celebrates homosexuality, such as pride parades, will be full of men wearing heels, dresses, makeup and all sorts of gender-non-conforming outfits. If you haven’t seen it before, it’s truly amazing to witness.
Aside from events celebrating queer pride, there is also the drag scene. According to Wikipedia, drag is defined as such:
Drag is a performance of exaggerated femininity, masculinity, or other forms of gender expression, usually for entertainment purposes. Drag usually involves cross-dressing.
Wikipedia
Most people have seen a picture of a man in drag with lots of colorful makeup, an extravagant costume and sparkly heels. It’s an art form that most people are at least remotely familiar with, but the imagery also happens to be strongly associated with homosexuality, regardless of the actual sexual orientation of the performers.
In some cases, it might even be what first comes to mind for people when they think of gender-non-conformity since images of it appear at least semi-regularly on mainstream as well as social media — regardless of whether in a positive or negative light.
Some people with certain political agendas might try to argue that all of this is a new phenomenon, among other falsehoods, born through easily accessible information and trends online that diverge from their heterosexual norm. However, that isn’t true in any way whatsoever.
No matter how they try to spin it, for centuries, there have been many well-documented cases of non-heterosexual men wearing gender-non-conforming clothing. A perfect example would be Philippe I, Duke of Orléans. As the brother of French King Louis XIV, one of the most powerful kings in French history, he was in an exceptionally well-documented and privileged position to be able to put his queerness on full display at court. He would often don women’s attire and flirt with other men at court. Since the Sun King, as Louis XIV was also known as, was quite fond of his younger brother, those men had to tolerate his flirtations if they didn’t want to fall out of favor with the king.
Philippe was born in 1640 and died in 1701 — hundreds of years before anyone now alive was even born. But I digress. The point I am trying to make is that gender-non-conformity has long been associated with queerness, and particularly with homosexuality.
Gender-Non-Conformity and Transgenderism
Unlike the association of homosexuality with gender-non-conformity, the topic of transgenderism hasn’t been a part of the mainstream discourse until fairly recently, even though, like gay men, they have always existed. As such, the association is only a relatively recent one.
The relation between gender-non-conformity and transgenderism is a much more complex topic than with homosexuality. That is because we first have to ask ourselves: When does it actually apply? A transwoman is clearly not participating in gender-non-conformity when wearing a dress and heels, but what about before her transition? If, for example, she has worn the same dress before or throughout her transition, when does it stop becoming gender-non-conforming? Or was it never gender-non-conforming in the first place even though she hadn’t yet discovered her true gender identity and still considered herself a man?
I suspect there is no right answer to the questions as it will vary quite a bit from person to person and their individual experiences. Some may say the latter is true while others may say it begins when they can “pass” publicly as a woman, and yet others may not classify it in such black and white terms at all. All of those views are equally legitimate.
One thing trans people and their allies would agree upon, however, is that a trans woman wearing clothing from the women’s department and a trans man wearing clothing from the men’s department is gender-confirming rather than gender-non-conforming.
So, am I gay or trans if I like wearing gender-non-conforming clothing?
Well, the short answer is a definitive “maybe”. I can’t answer that question for you as everyone’s situation is different. What I can tell you, however, is that just because you enjoy wearing a skirt and heels doesn’t automatically make you gay, trans, straight, cis or anything you weren’t before you put them on.
Discovering an interest in them may be an indication that you feel like more of a woman than a man and therefore sets you on a path towards discovering your true gender identity. Likewise, they may be a gateway into one of the gay scenes where you discover your attraction to other men. Just as likely, though, is that you just simply like the way the clothes look or feel, or even the “rebellious” nature of wearing them, but remain comfortable as a heterosexual, cis-man.
I’ll repeat it again for good measure because it’s important: wearing clothes doesn’t make you straight, gay, trans or anything else. They may help you discover yourself or feel more at ease with yourself, but you are still you no matter what you wear.
Conclusion
In the end, this is a question that most of us men who wear “women’s” clothing are subjected to, whether internally or externally. It’s unfortunate and it shows just how ignorant most people are of the subject.
It also shows a pattern so repetitive that it’s nauseating. Society does not like men doing anything that is overtly feminine, such as wearing a dress with tights. It makes them appear too feminine which is to say too weak and not “manly” enough. It’s blatant misogyny as anything female is dismissed as being below a man’s manly manliness. Instead, with gender-non-conformity’s long association with homosexuality, it’s easier for those not inclined to much mental exercise to quickly make the connection to queerness and stuff the gender-non-conforming man into a rainbow-colored box and call it a day’s mental work.
The danger here, however, is that you allow yourself to be talked into thinking you’re something you’re not. I speak from my own experience having gone through a long, diffiducult phase where I questioned my own gender and nearly lost my wife.
There is one last thing I would like to mention before I wrap up. While I’m not homosexual or trans, it is certainly an honor to be associated with such a wonderful group of people who are brave enough to be themselves in the face of so much discrimination and ostracism. So, while I don’t consider myself to really be a part of the queer scene, I definitely consider myself an ally.
Wearing gender-non-conforming clothing does not mean you are anything you weren’t before you put the clothing on. It may lead you to discovering that you are gay or transgender, but it’s just as likely that you put the skirt or dress on because you simply like wearing them. Don’t let yourself be pressured by others or by society at large into thinking that you’re something you aren’t. Stay true to yourself, no matter your gender or sexual orientation, and enjoy the wonderful freedom that comes with wearing clothes from both the men’s and women’s departments!
What are your experiences? Have you ever been asked or asked yourself if you’re gay or transgender just because of your choice of clothing? Let me know in the comments!
Note: For any German speakers here, I just released a translated version of this post on my German blog, Alex’ Notizbuch.