Of course a man can wear a dress, though it ideally should be tailored to fit him

Rachel Saunders
5 min readMar 14, 2023


There is a running argument about men wearing women’s clothing dating back to at least 600 BC that states that such a thing is an abomination. Literally there in black and white, translated into all the world’s languages that for a man to wear women’s clothing it is a grave sin. In the same vain as wearing clothing made of mixed fibres and burning offering to false gods. This whole discourse springs from a desire to enforce a binary understanding of masculinity, that men should be men and never sullied by the feminine. That what constitutes women’s clothing is forever shifting depending on culture and time always slips the attention of those decrying skirts, dresses, and make-up. For clothing to be worn by men it must be declared masculine by men so that other men know that it is in fact okay to be seen in those garments.

The fact that women can wear men’s clothing without significant blowback, unless you are on the outer edges of butch or live in rigidly patriarchal cultures, says as much for the contradictions of fashion and the enforcement of gender expressive binary. For a man to look like a woman is degrading, yet for a woman to cut her hair short, wear jeans, put on plaid and drink beer is somehow empowering. This power dynamic, the idea of what is in and what is out, essentially reinforces both the superiority of all things apparently masculine, while at the same time relegating femininity and womanly things to frippery and ornamentation.

So far so second wave feminism. What marks the 2023 version of this line of reasoning as so bellicose is that it is more than inherent reaction to changing fashion trends. It is a deliberate attempt to legislate a binary understanding of whatever the enforcers view as masculine and feminine. That men in Scotland and Indonesia were kilts and sarongs is a matter of fashion semantics, this clothing is deemed masculine because men say that it is masculine. Those who seek to ban drag shows, and purported cross dressing, fail to see that assigned women at birth also perform drag, and so will they arrest an assigned at birth woman for wearing drag and telling a story to kids in libraries? Who gets to decide would be in the eye of the arresting officer.

Contradictions in clothing are nothing new. It is as old as recorded history, with instances in Babylon and ancient China baked in clay and on bamboo tablets. What we wear is a profound statement of who we are as people. Our cultures, our fashion industrial complex, our media saturate us every day with images of what we should wear, or what we should not. That Harry Styles can be considered the world’s best dressed person says as much for position as a celebrity as it does for the way we place him on a pedestal. That none of the clothing he wears was necessarily tailored for him, or tailored for other men, shows that fashion designers are not ready to push that style into the mainstream. Even Billy Porter is simply a moment rather than a movement.

Which cuts to the heart of this piece. Men, and newly emerging trans women, struggle to find feminine clothing because it is simply not mass designed for their shapes and sizes. Many assigned at birth women have the same issue, but the breadth of brands and marketing aimed at them makes it easier to find at least one brand that will fit more or less. Men on the other hand are never catered for, never give the range of dresses, skirts, blouses etc that would suit their body shape. Much of the issue of pastiche comes from the fact that the tailoring of femme fashion was not aimed at them.

Femme clothing is designed to be over engineered, less practical, and to a point restrictive. It is meant to keep those who wish to wear it in a position lesser than those who wear masculine garments. This is not to say that those who wear feminine attire feel restricted or lesser, but the signals those clothing radiate to others is a matter of perception. A man choosing to wear restrictive clothing stands out, makes himself something other than his peers. He becomes somehow lesser. That this is a logical fallacy only underlines just how absurd talk of banning so called crossing dressing really is. If a man wears a dress it inherently becomes a manly thing. Does it become a masculine garment, or does it retain residual femininity? That is the more complex and intriguing question.

Or does it really matter? Go back far enough in history and all clothing has been worn by all gender identities at some point in various cultures around the world. Each culture has its own myopic version of the gender binary, seeing what it wants in masculine and feminine. To impose a cultural perspective on this shows our own biases and religious mores. That some cultures feel the need to legally impose a version of the gender binary is a sign of cultural insecurity. Fashion ebbs and flows, and whatever each of us chose to wear should be both a matter of personal taste and whether the clothing suits our figures.

This last point is always the one that drives me deeper into engaging with fashion. Each of us has a sense of style and personal choice. Unless you have significant wealth we each have to each do with what is sold to us in clothes stores or charity shops. Cerulean blue was chosen for Andie’s sweater long before she brought it, and the garments we wear are dictated by creative forces far outside our control. If you do not like this season’s offerings your only choice is to not purchase it, or make the clothes yourself. Thus, when designers have to offer styles that will sell they are limited to what they believe society will purchase and chose to wear. If you fall outside that broad demographic, you are stuck.

Salmon pink had a moment in the sun, then became part of men’s fashion in the late 1990s. It added into the colour pallet a splash of something soft that until then was relegated to sweet sixteens and ballet dancers. This small example of changing trends and tastes highlights to evolution of what is masculine and what is femme. For a man to wear pink is no longer a fringe affair, simply just Mike picking a shirt and tie from his work wardrobe. Add cufflinks and a pocket square and he is still masculine without overstepping into being an abomination.

Obviously, this is as complex as the societies we live in. There is no one way to be masculine or feminine, and to attempt otherwise rejects the beauty that is being human. Drag bans, clothing restrictions, and walking while trans all stem from the same desire to impose a mistaken understanding of binary gender expression. And the majority of people who will be caught out will be heteronormative cisgender folk who simply wish to be themselves. If a man wants to wear dresses and skirts on the daily then all power to him, just please make sure that it is comfortable and fitted to your figure, as it will make you feel so much more at ease with the clothing.