Gender expression and fashion have long been intertwined – after all, many of the indicators people use to identify someone as a particular gender are based on things like hair, dress, and the presence of makeup (or the lack of it). Whether cis or trans, everyone tends to perform gender to some degree. In fact, many people found that quarantining during the pandemic made them realize they weren’t as attached to performing their assigned gender as they thought, and it gave them the chance to explore their gender identity away from prying eyes. With all this in mind, today we’re going to look at:
- Gender expression and drag
- Cultural differences in gender expression
- Ways you can express your gender through fashion
I’m (Drag) King of the World
How Drag Has Been Utilized By Both Cishet And LGBT Communities Over Time

Drag has been around for millennia – in Menaechmi, an ancient Roman play by Plautus, Menaechmus I puts on his wife’s dress, intending to smuggle it out of the house and deliver it to his mistress, and declares to the character Peniculus, “Look at me. Do I look the part? [...] Tell me I am gorgeous.” Further, in Elizabethan theater, because women were not allowed to perform, all female roles were performed by men in drag (with drag itself being a term that has existed since 1388). Even with those strict codes, playwright Shakespeare toyed with the idea of gender in his plays, with crossdressing being a key theme in As You Like It and Twelfth Night.
The first recorded drag ball in the U.S. was all the way back in 1869, known as the Hamilton Lodge Ball, and was an annual event up until 1937. Hamilton Lodge #710 of the Grand United Order was formed in 1844 by a group of free Black men who had been rejected from forming an aligned lodge with the American Odd Fellows, and in 1869, held their first annual Masquerade and Civic Ball, the first recorded ball in Harlem where men dressed as women.
These balls were originally organized by straight men, but over time, became a way for non-straight people to appear publicly in drag. Both men and women performed drag, and despite cross-dressing being illegal, the balls were actually protected and officiated by the NYPD for a time, due to the flourishing popularity of the Pansy Craze. However, toward the end of Prohibition and the beginning of the Great Depression, anti-LGBT sentiments emerged, along with a sex-crime panic. Because of this, police turned on drag performers and began arresting them, forcing them underground.
Drag has thankfully been on the rise, though, and for good reason – for cis and trans people alike, drag allows you to tap into facets of gender you’d like to explore, and exaggerate them. And for trans people, it’s a good way to express yourself amongst other like-minded people, without worry of rejection for dressing in a socially frowned upon way, or not passing in a traditional sense.
Cultural (And Historic) Differences in Gender Expression
What’s True In One Place Isn’t True At All In Another (Or Even Another Time)

Long Hair – Not Always Feminine
Gender expression and norms vary from culture to culture – for example, while in many European cultures, long hair is considered feminine, this isn’t the case everywhere. Many (though not all) indigenous cultures consider long hair to be neutral, with many masculine-presenting indigenous men wearing their hair long. Even in the American military, where the “Induction Cut” is commonly known, short hair wasn’t always required, and long hair wasn’t inherently associated with femininity. Instead, regulations were put in place to control lice outbreaks (and eventually made stricter to promote uniformity). With the rise of gas masks, the shaving of facial hair was also required in order to ensure a proper fit.
Long, Flowing Clothing Was And Is Neutral – Or Even Masculine
Long clothing, especially colorful clothing and clothing that resembles dresses, is often considered feminine in modern western culture, but not everywhere (and not even in places like historical Europe). For example, kaftans are robes originating in Asia that have been worn by many different cultures for thousands of years. In some cultures, kaftans were predominantly for men, while in others they were unisex (which is how they’re often treated today). Similarly, the West African agbada originated as a garment for rich Yoruban men, but is now considered unisex, and is no longer exclusive to Yoruba culture.
The History Of Makeup Over Time
Interestingly, makeup was also considered gender-neutral for a long time, and commonly worn by men – it wasn’t until the mid-1800s that social views of makeup shifted, as Queen Victoria I and the Church of England declared it cosmetics “vulgar” and “an abomination,” linking makeup to vanity, femininity, and “the Devil’s work”. Before then, men in England, France, and even ancient Rome used powders to lighten their skin, and men in ancient Egypt used makeup to do everything from invoking the gods to communicating wealth and status.
In the 20th and 21st centuries, mens’ makeup usage has made a gradual comeback – since the 1930’s, male actors have been wearing makeup, and the 1970s and 1980s saw a rise in male musicians like Bowie and Prince wearing makeup and flamboyant clothing, later succeeded by emo and pop-punk musicians like Pete Wentz wearing eyeliner. It was at this point in the 2010’s that makeup companies started advertising towards men, and today it’s growing even more popular for men to wear makeup, though it’s still viewed as gender-subversive or a sign of non-conformity.
Pants Are Normal For Women Now
Though women have historically worn pants across different cultures, much of modern history restricted it, both with overt anti-crossdressing laws, and laws against “vagrancy,” in which individuals were not allowed to be “disguised” in a way that prevented identification (with dressing outside of gender norms constituting a disguise). Through much advocacy, these laws and requirements have mostly been abandoned, and now in many places, it’s far from unusual to see women wearing pants, and is no longer considered inherently masculine. Some forms of long pants, such as leggings, are even seen as inherently feminine.
Expressing Your Gender Through Fashion
Mix And Match Everything You Like, Creating A Uniquely “You” Presentation

Gender expression means something different to everyone. From culture all the way down to the individual, there are so many different factors that go into gender expression – for example, I’m a transmasculine individual on T, and I’ve found joy lately in dressing in ways that accentuate femininity, because I enjoy being read as a gender non-conforming man (where pre-transition, I worried about being read as a cisgender woman). Similarly, there are transfeminine individuals who enjoy presenting in a more masculine/butch way.
The key to expressing your own gender through fashion is figuring out what you’d like to highlight – are you shooting for a masculine look? A feminine look? A combination? There are several ways to tweak your fashion presentation, including:
Hair
Hair is, of course, a big one – generally, in the west, long hair is associated with femininity, but it can be used to tap into both your masculine or your feminine side. You can even experiment further, having long hair with a “masculine” cut, or short hair with a “feminine” cut, playing around with how they accentuate your features differently.
Clothing
Clothes are a great way to tap into different aspects of your gender expression. To tap into your femininity, skirts or crop tops can be a great start – depending on the culture you live in, colorful clothes can also be associated with femininity. Meanwhile, you can try dressing more masculinely through the usage of button-downs, suits, etc. Mixing and matching these presentations can come up with some great androgynous looks, and you can even throw in some accessories like hair clips, purses, belts, carabiners, etc.
Makeup
Makeup can be great to express your gender in either direction – obviously it can be used to express femininity, but used the right way, you can also use it to look more masculine. It’s a great way to get out there as subtly or as loudly as you want, and of course, it’s easy to remove if you don’t like the look or are done with it for the day. Because of this, it’s great for expressing your gender even when you’re in a situation where you can’t express yourself the way you’d like all the time.
That’s it for our deep dive on gender expression and fashion – we hope you’ve learned something new today! Feel free to get out there and experiment, or check out how others experiment.