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How Dressing More Masculine Taught Me to Tap Into my Femininity

Two women sitting on a skate ramp with a skateboard in hand, dressed in masculine clothing with long hair

I’ve always been inclined to dress more on the masculine side. Growing up, I was a tomboy and always wore my older brother’s hand-me-downs. As an athletic, young, closeted queer I felt more comfortable expressing myself with baggy t-shirts and rugged jeans than in tight skirts and painted lashes. But, as I aged into teenagerhood, I left that behind in favour of fitting in.

In your early teens, especially as a member of the LGBTQ2S+ community, it can be easy to throw aside your style preferences in order to blend in with more mainstream looks. But, as I grew older and learned to embrace my queerness, I found ways to not only lean into a more masculine style, but to use that in order to tap into my femininity. Adopting looser-fitting fashion choices offered up new avenues to explore and express myself through makeup, nails and accessories by reworking quintessentially feminine pieces in creative ways.

Thanks to artists and style icons like Billie Eilish and Zendaya, who have mastered the art of androgynous fashion with baggy tees and sleek suits, masculine and gender-bending trends have been on the rise for quite some time now. From baggy cargo pants to the androgynous bleached brow, there are so many ways for people who were raised female to explore a more nuanced gender expression.

Related: Law Roach’s most memorable celeb stylist moments.

As someone who has learned to embrace that androgynous style, here are five ways that dressing more masculine taught me to tap into my femininity.

Side angle of a woman in a black suit in front of a white backdrop

Playing with proportions

In the early stages of embracing my queerness, when I first felt validated in expressing myself with a more masculine style, it was easy to turn away from femininity entirely. After being closeted for so long and conforming to a feminine wardrobe for most of my life, all I wanted was to head to the opposite side of the spectrum and solely embrace a masculine style. But, as I grew and understood myself through a more nuanced lens, I began to uncover a feminine side of myself that I had ignored for a long time.

The key to pulling off a more masculine style has been all about finding the cuts and shapes that work for me.

So, once I figured out how to properly style the more masculine pieces in my wardrobe, I began to find freedom by offsetting them with quintessential feminine accents. From layering with sheer tops to donning some tear duct liner, I slowly uncovered countless ways to use fashion to play with and redefine my relationship to my gender expression.


Ultimately, changing my style taught me that finding the right cut for your body type is key. From investing the money in a well-tailored suit to matching an oversized top with trousers that fall right to your ankle, androgynous fashion is all about balancing the right proportions. Men’s clothes are obviously intended for a masculine body shape, so as someone with feminine proportions, the key to pulling off a more masculine style has been all about finding the cuts and shapes that work for me. Once I discovered that, it unlocked new ways to play with layering and I was able to style feminine pieces in balance with my more androgynous statement looks.

Related: 10 stylish, body-inclusive outfits inspired by Lizzo to shop now.

Closeup of an eye with graphic, colourful liner

Using makeup for the sake of creativity — instead of what’s popular

Once I allowed myself to play with my gender expression through what I wore, I rediscovered a love for makeup. With the rise of bright eyeshadows and graphic liner, there began a cultural movement toward using makeup for creativity instead of simply hopping on trends.

As Euphoria —which primarily revolves around queer characters — has soared in popularity, subversive trends like sparkly tear drops and the early 2000s goth girl aesthetic have come to the forefront. This movement has given queer people and those embracing an androgynous style an opportunity to really channel the artistic aesthetics of makeup to use it as a unique form of self-expression.

By learning to love makeup again while staying true to a more masculine wardrobe, I found unique ways to brace femininity as a form of self-expression and identity, rather than as a style and stereotype I had to conform to.


Related: What is the cost of unrealistic beauty standards? Unfortunately, it’s billions of dollars a year.

Nails with colourful, squiggly nail art

Hopping on unique nail trends

Similarly to makeup, when I began to feel more comfortable in my gender expression, I found new ways to embrace nail trends as a form of expressing my identity. With unique, flashy trends like aura nails and velvet manicures, it’s been freeing to find creative styles that feel like they fit with who I am.

I’ve also found that playing with nail styles really offers a unique way to lean into that feminine energy, without having to disregard or throw aside a more masculine clothing style.

See also: Hailey Bieber’s chocolate glazed-donut nails are a delicious look for fall.

A hand on leather pants wearing chunky silver rings

Accessorizing in new ways

Honestly, there’s a lot of freedom in accessorizing for a masculine wardrobe. With boxy neutrals and baggier bootcut jeans, I found an opportunity to lean into bag shapes and jewelry styles I had never considered before.

Embracing a more masculine style has taught me that fashion should really be all about dressing in what makes you feel most like yourself, regardless of trends.

From chunky chains to thick rings to sleek messenger bags, simplifying my wardrobe presented a path to accessorizing for myself rather than for trends as well, which ultimately allowed me to express my femininity through distinctive accessories that I identify with.

Two women leaning on each other in hoodies

Ultimately, it’s all about wearing what makes you feel most at home

All in all, embracing a more masculine style has taught me that fashion should really be all about dressing in what makes you feel most like yourself, regardless of trends.

Over the last century, fashion has been transforming at rapid speeds, eventually reaching where we are today — which is all about dressing how you want.


If there’s one thing I’ve learned in my fashion journey, it’s that style should truly be about embracing your identity, whether that leads you to dopamine dressing to improve your mood or dressing androgynously to put your gender expression at the forefront.

You may also like: Then and now: 10 drastic celeb style changes.

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