My Journey into Skirts

My Journey into Skirts

Tags: People Story

…and other "fem" things.

It feels silly to write about how I began wearing such a basic garment. And yet here we are, in a culture where so much of the population avoids skirts.

This story is a reflection on what drew me toward feminine expression, the forces that held me back, and how my life changed in the process.

Let's start at my Grandma's pool, Summer '92. I was fresh out of the water and cookies were inside, waiting. I could have drip-dried but tying a towel around my waist sped things up. Being in this long cloth wrap felt different… breezy, exotic, maybe empowering.

I'd leave it on a bit longer than necessary. Wearing something that bordered on feminine was a rare opportunity as a seven year old boy. I remember asking myself, 'Why can't this be a normal thing?'

Growing up in a small, white, rural town in the 90s had its influence. Sexism, homophobia, transphobia, and other forms of toxic masculinity were the norm. I avoided most things that could be considered "unmanly". Expressing femininity around schoolmates could lead to months of ridicule. Not that I had an urge to wear skirts just yet  –  the patriarchal burden was pervasive. Trying not to care too much about fashion, my teenage self mostly went along with the baggy, skateboard brand clothes.

On a middle school band trip, I let a convincing friend put her eye makeup on me. It was more tense than fun. I wiped it off after a minute or two, afraid the boys might notice.

Skirts really only crossed my mind a couple decades later. Before this, a few experiments and costumes started desensitizing me to feminine expression.

My first leggings were for a 'sweater/jeggings' holiday party. I was pleasantly surprised by their light and stretchy feel.

A picture from a holiday party of me in jeggings, and a sweater with LED lights on top. More jeggings in the backgrouns, and a pile of jeans on a couch.In jeggings (jean leggings), Dec 2010

I got a perm in my mid-twenties, though it was for a masculine halloween costume (Seth Rogen in Pineapple Express). The next year I grew my hair out and dressed as Russell Brand for halloween, who seems comfortable expressing femininity. It was the most fun I’d had in a costume. A friend put eyeliner on me and back-combed my hair into a poofy mess. I had a pile of necklaces, rings, and belts to top it off.

Left: me getting a perm at the hairdressers — big bubble shaped machine around my head; Middle: Me sitting on a couch with a perm, in a suit, holding a beer can, photoshopped into a scene from movie ‘Pineapple Express’; Right: Going as Russell Brand for Halloween, standing in a kitchen with tight black clothing, messy and poofy hair, and many necklaces and rings.
Left: Getting a perm, Oct 2008; Middle: With perm, photoshopped into a movie scene, Halloween 2008; Right: Going as Russell Brand, Halloween 2010

In my late twenties two of my Scottish friends got married. I was able to experience the open, airy freedom of movement that kilts offered. Suits were stuffy in comparison. And those twirly dance moves, all under the safety of cis masculinity with which I identified.

Me in a blue/green/black kilt, with white shirt, black vest, sporran pouch, thick white socks, and open black dress shoes. I’m making a ‘call me’ gesture with one hand, while leaning and stepping on a structure.
In full kilt getup at my friend’s wedding, May 2012

Starting a few years later I'd occasionally wear my very own kilt  –  a gift from my dad who created a family tartan pattern.

It wasn't until my early thirties that I bought my first clearly fem garment. I must have been feeling extra secure that day while browsing a thrift store in Vancouver. I was with some of my best friends who encouraged me to buy these stretchy women's pants:

Me laying on back of a couch at Otherworld regional burn festival, with trees and mountain in background, giant bird cage bicycle behind, and others sitting on the couch.
In my flower pants at Otherworld

They had a flower pattern and were somewhere between capris and tights. I'd put them on for a dance or festival and with compliments I eventually wore them everywhere.

Later that summer I was looking through clothing racks at Burning Glam  –  a 'theme camp' at a regional Burn that provides free (for keeps!) clothing and costume wear.

Me in a forward stance, with a red/orange/brown striped sarong, with brown ties at the top, and wearing black tights.
In my mesh sarong skirt

I came across a mesh skirt that looked somewhere between a sarong and costume prop. I loved wearing this around, mostly to festivals at first.

I was leaning into new styles. Leggings had become more popular with men. It wasn't too stretch-zone for me to try the more fun 'feminine' patterns. Over time I found myself defaulting to the women's section in thrift stores  –  first for leggings, then capri pants, sweaters, and shirts.

For a while I felt a strong pull to balance any feminine item with masculine clothing, body language, or attitudes. Shedding this and my own layers of misogyny takes time.

In late 2018 I was considering the possibility of owning a skirt. While perusing a vintage clothing store this long, flowy skirt presented itself:

Long, thin skirt on clothing rack. Paisley patterns with orange, red, blue, cream, and black colours.
My first skirt purchase

It fit perfectly, which was not exactly a relief. No excuses.

With a trippy paisley pattern and its own matching belt, I had to at least try it on. Going into the change room with a skirt felt strange, even if the staff seemed open-minded. It fit perfectly, which was not exactly a relief. No excuses. I made the purchase, thinking there'd be some event I could wear it at  –  that or I'd give it to a friend.

It took months to let myself be seen in the skirt. With gentle encouragement from a friend, I broke the seal and wore it to a dancey event in Victoria. Not just any event  –  one where people often wear playful, sensual, creative getups. The vibe at this type of event is respectful and accepting.

I paired the skirt with a white crochet lace vest from the thrift store. At the time it was the most feminine outfit I'd worn in public. Nerves were present and quickly overridden by approving smiles. This created freedom to dance and be in this new possibility.

I loved wearing this skirt to the odd dance or close friend gathering. But most of the time it felt vulnerable, out of place, or too fragile and long. I was kinda stuck.

Around this time I ran into a friend of friends while out for lunch. I'd seen him with fem clothing before and he was wearing a kilt on this day. Sitting one table over, I overheard him tell a story about a confrontation over his fem clothing. He called the man in and asked things like, 'What does masculinity mean to you?'. This diffused a tense situation with an opportunity to learn and connect.

I was feeling inspired and hopeful that I could one day honour my self-expression in any scenario. After lunch I went straight to a thrift store and found my second and third skirts.

Spinning with red/yellow/grey/orange flower patterned skirt, and black tights.
My second skirt

One of them had a flower pattern with folds of extra fabric near the bottom, almost like a kilt. This tinge of masculine helped me bridge a gap. I'd default to this skirt in new environments, like certain public places, co-working meetups, and family visits.

Later, the same person I ran into at lunch posted online to recommend a book called The Will to Change, from bell hooks. I picked up a copy and read about why men suppress their emotions. I got a better understanding of how the patriarchy is destructive and limiting to those affected by toxic masculinity. It helped me notice socialized thought patterns and behaviours. Like the ones that kept me from expressing femininity. I could more easily consider the choice between fear and things like beauty, sexuality, and playfulness.

At this point I had a few feminine outfits and a little more confidence. A friend's (mostly fem) clothing swap bagged me some great tops and a frilly skirt  –  things I might have skipped over at a thrift store. These were perfect for circling my comfort zone on a night out.

Accessories were on my radar too. I would try them at festivals, costume parties, dances, and then smaller gatherings. I got my ears pierced with the vision of having big, dangly fem earrings. I'd borrow eyeliner and mascara. Friends would paint my nails or lend me a bralette and necklace. Eventually I purchased my own things, including a black pair of tights which was a game-changer in its skirt compatibility.

Regardless of what I had access to, it took time to feel safe showing up with certain feminine garments or traits. High heels are still elusive to me.

Single horizontal line graph with arrow pointing right, showing small pink/black dots along the line, representing easy to difficult fem traits to show up in. From left to right: Beach towel wrap, leggings, painted nails, eyeliner/mascara, crop tops, thick mid-length skirts, scrunchies, long flowy skirts, eyeshadow, purses, mini skirts, bralettes, dresses, high heels.
Fem garments/traits on average, from easy to daunting (for me)

My sense of safety depends on the context too, based on how expected a behaviour is and how open-minded the people are. These two main factors can interrelate, and shift with exposure. Below is what that looks like for me, with the average skirt, and average event  – for example, I stick to festivals that encourage open-mindedness.

‘Social Safety: Skirts’ graph. X-axis ‘Closed minded’ at right, ‘Open minded’ at left; Y-axis ‘Unexpected’ at bottom, ‘Expected’ at top. Bottom right: in red circles: Golf Courses, Rodeos, Parent’s house, Places with anti-trans/anti-gay laws. Top left: Theatre in orange-yellow. In bottom right, Downtown, Work meetups in orange and yellow-green. In top right, Live music shows in yellow-green, and Friend gatherings, Costume parties, Festivals, Home with partner in green.
Some of these are more or less hypothetical for me, like rodeos

Through first and second-hand experiences, I grew my confidence and progressed through many of these settings, starting at the top left of the graph.

My wardrobe still didn't match my excitement though. Most of it was stereotypical masculine and didn't go well with skirts, but I was starting to let go of these items.

Creating new looks takes time, energy, and usually money. My process was fairly organic but required a push here and there.

After moving to a rural area, I used my privilege of time and funds to buy ten skirts at a big thrift store on a trip to the city. This was a massive boost I wish I'd done sooner.

Having an assortment isn't enough though. I realized that tops can make or break a skirt. Most of my sweaters paired well with them, but my t-shirts didn't. I found longer tunics, fitted tank tops, and cropped tees to all compliment a style that felt deeply personal. Outfits were becoming so creative and fresh.

As for hiking gear, most is fitted and gendered but I learned that lightweight skirts are great for backpacking  – at least in places with few mosquitoes. They're more airy and breathable than any pair of shorts I've owned.

Myself: White 37 year old with pony tail, wearing pink skirt, blue t-shirt, backpack and hiking pole, on a wooden boardwalk in the trees on the top of small mountain. Blue sky and clouds.
Hiking the North Coast Trail, Vancouver Island, Aug 2021

Shopping isn't always easy. Clothing websites divide people into one of two genders at the first click. Physical stores use completely separate sections, floors, or even buildings. These classifications can be oppressive for anyone: non-binary folks looking across, between, or beyond the binary; men and women whose gender is affected and reinforced by fashion trends; and anyone whose figure aligns more with a gender they don't express.

I haven't figured out size conversions yet. On top of this, women's shirts and pants that fit me in some ways can be too tight at the shoulders and groin, or short in the arms.

Thankfully, skirts don't discriminate on body shape, for the most part…

The 'male bulge' on tight, stretchy skirts doesn't fit the flush female look that society teaches us is "normal". It bothered me at first, and still does a little. Not wanting to tuck or wear tight underwear led me to other solutions:

  • Longer shirts or sling bags that cover the bulge
  • Thicker fabric skirts that flatten it
  • Belly-high skirts that fall straight down in front
  • Fabric folds, frills, textures, and patterns that hide it

Grid of 10 pics of my lower half. Top row: Purple skirt, orange sling bag, black tights; Black/red skirt, spinning with long red shirt, brown tights; Black skirt w/ white dots, black tights; Black mini-skirt, long yellow shirt, black vest/tights; Frilly grey mini-skirt, black tights. Bottom row: Vintage blue/red/green pattern, yellow shirt, brown tights; black mini-skirt, blue tunic; red/black skirt; black mini-skirt, red umbrella tights, long purple shirt; thick black flower skirt, green tights
Skirts, tops, and sling bags can conceal certain male anatomy.

A kilt happens to do all of these things. It's made of thick, folded cloth with a tartan pattern. They're worn well above the waist and attached to belt loops is often a sporran  – a fur or leather pouch that hangs in front. This also doubles as a pocket, which few skirts have.

Western fashion rant

Kilts can be fun but their 50 square feet of wool cloth is warm and heavy for dancing. They aren't accessible either  –  expensive, formal, and often thought to be reserved for Scottish, Irish, and Welsh men. They're the only widely accepted skirt in western men's fashion, and still rare.

Once in a while I see the less formal 'utility kilt' which borrows some of its features from carpenter's pants. They're usually worn with rugged boots for a practical, ultra masculine look that bucks any question of femininity.

Many still consider skirts to be for only one of the binary genders. The Oxford English dictionary would have to agree:

Google search for the word 'skirt' which brings up a definition: a garment fastened around the waist hanging down around the legs, worn by women and girls.

Men in skirts or dresses has often been seen as or avant-garde, high fashion, or for rock stars only:

From left to right: Freddie Mercury with shiny black skirt, black tights, and high heels; David Bowie on stage leaning into a stand-up microphone that he’s holding, with long shirt and matching skirt + pants, all gold and red; Iggy Pop in black dress, holding a grey/white purse in one arm, withquote “I’m not ashamed to dress ‘like a woman’ because I don’t think it’s shameful to be a woman.”; Anthony Keidis in shiny sequin black/silver skirt, shirtless, singing into microphone on stage.
Left to right: Freddie Mercury, David Bowie, Iggy Pop, and Anthony Kiedis

And while it's common in many cultures for men to wear skirts and similar attire, the western gaze shuns the behaviour. Unless it's done as a lark. Media has portrayed men in feminine clothing as either gay, opportunistic, or insane.

It's like we forgot that most gendered traits in western fashion were neutral and flipped at various points in time:

  • There's a long history of men wearing skirts until the 14th century; pants were only first created for horse riding and cold weather
  • High heels were first worn by men
  • 'Pink for girls, blue for boys' was neutral or backwards for long stretches of time before solidifying in the mid-century
  • It was once illegal for women to wear pants in many cities, and it's still frowned upon or banned in certain places like private schools
  • Men in pink dress shirts, now common, was somewhat taboo as little as twenty years ago

This all reminds me of a meme I saw a few years ago:

Two images side by side. Left: White, middle-aged masculine person in 1940’s suit, holding a hat, walking down sidewalk, in black and white, with ‘1948’ in white letters at top; Right: White, masculine younger adult on bus or subway with white toque and sunglasses, pink and yellow sweatshirt, ping/blue/white tights, and white/red high socks with ‘MEAT’ in vertical print, with ‘2018’ in print at top; White lettering over entire image: ‘Men: What the hell happened?’

To which someone replied:

Two images side by side. Left: White king posing with cane, large white/blue/gold dress/cape, light blue tights, red high heels, sword, and long black curly hair or wig, with ‘1715’ in white lettering at top. Right: White, middle-aged masculine person in 1940’s suit, holding a hat, walking down sidewalk, in black and white, with ‘1948’ in white letters at top; White lettering over entire image: ‘Men: What the hell happened?’

I can appreciate both memes, and the joke that men's dress has been in decline since the 1700s. Maybe it's becoming more fun, recently… who knows?

What we consider masculine changes over time. Influencers have shifted culture, like royalty, celebrities, brands, and show biz. Capitalism and politics play a huge role.

It's all interrelated, creating a society that divides gender from the waist down to support patriarchal ideas, as Antonia Ceballos describes:

"Skirts, even today in many minds, represent femininity as accessible, penetrable, open, domitable and submissive, the idea of femininity as fair, little, pretty and weak; femininity as irrational and incapable of self-governance. In stark contrast, pants in plain sombre colours symbolized male rationality, domination and power in culture and politics." (Quora)

Author and scholar Jo B. Paoletti simply puts it:

"For a man to adopt something that's feminine is seen as giving up his power."

Lack of vulnerability and other masculine stereotypes are incredibly damaging to men. They have much higher rates of violence, suicide, and risky behaviour, alongside a reluctance to seek out preventative care and mental health services (infographic + article). And these are just some of the direct effects.

Reconsidering gender

Somewhere in exploring how I want to show up in the world, I realized I no longer identify with so-called masculine qualities any more than feminine. A feeling built up inside me that needed to let go of gender-based expectations and push back against these dynamics.

Coming out as trans/non-binary earlier last year has given me more freedom. One thing that made it a tough decision was wanting to help show that men can express femininity. I thought if I moved away from manhood, I couldn't do that. But I still am. I talk about these things. And I show up in ways that could make strangers think I'm a man –  I often have facial stubble, and use the men's washroom.

Among other shifts in mindset, identifying as genderfluid/queer (vs. a gender non-conforming man) gives me belonging. I can more confidently appear anywhere between or beyond the binary genders. Instead of trying to complete a fem look, I can feel comfortable in my body mixing feminine and masculine clothing in the same outfit. I might look androgynous on some days, though I'm still figuring out what that means, with society's 'masculine is default' messaging.

Navigating oppression

In public I've had mostly pleasant interactions around my gender expression. The people who comment seem stoked about it. The odd person is genuinely inspired and a little mind-blown.

But I can't say it's all been good.

I often consider what type of people I might run into. Dressing more conservatively in pants is something I've felt the need to do. This comes up when I'm meeting someone in a power position, like a landlord or a person who's selling something in high demand.

Occasionally I'll get a confused or disapproving look, almost exclusively from older cis white men.

I was once asked by a man in the grocery store if I was smiling under my mask. It was the first time I got to experience this uncomfortable thing women regularly face (men: stop asking women to smile).

Then there's the fear of violence or 'trans panic', coming from a man's masculinity being threatened, transphobia, homophobia, etc.

If I plan ahead, the 'cis white male' look is something I can fall back on, without excessive gender dysphoria. This is a privilege and safety net I'm learning to use less and less.

The toughest part about my new gender expression and identity has been parental rejection. I've received gaslighting, guilt tripping, emotional blackmail, even an ultimatum.

Initially they showed avoidance, denial, and sometimes poked fun. This evolved into guilt, shame, sadness, confusion, repulsion, protectiveness, and intolerance. They see my wearing skirts around them as a sign of disrespect, and would rather oppress my self-expression than look at why they feel discomfort.

Social bubbles and decades of conditioning can make someone choose judgment and control over acceptance, open-mindedness, and critical thinking. Knowing this, it's easier to work with their behaviour and sit with my own feelings of hurt, anger, and disappointment.

I'm trying to show compassion in these relationships by building mutual understanding. To help demonstrate how certain beliefs or reactions are oppressive, bigoted, and just plain bonkers, I ask things like:

  • What makes a skirt better suited to certain genders?
  • Why is it a bad thing to dress like a woman?
  • What do you like about gendered dress codes, and why?
  • Why is 'weird' a bad thing?
  • How would you define masculinity in a way that excludes women?
  • What are your guiding principles that help you decide whether something is okay, or on the right side of history?
  • How does this change our relationship, or me as a person?


Though it's only been a few years, my progression into skirts has felt strangely gradual. Looking back, it's hard to imagine the nerves that told me to hesitate.

I'm not sure what I'll be wearing in the future but it's been fun making up for lost time. Nothing's set in stone and there's so much wonder in questioning our culture and dress.

There is potential for physical and psychological harm, at least in some settings. But the more people do it, the safer it becomes.

My advice to non-women who are considering skirts:

  • Tie a towel around your waist at the beach
  • Paint your nails or try other fem accessories
  • Borrow a skirt for a dance, costume party, or festival (when covid allows) – wearing one here alone is a powerful act
  • Try clothing swaps or thrift stores and grow your wardrobe
  • Follow celebrities and influencers, like Jaden Smith, ALOK, Harry Styles, Lil Nas X, Billy Porter, Shaneel Lal, Geo Soctomah Neptune, Troye Sivan, George Tyrone, Mark Bryan, and Jorge Dugan
  • Get inspired by women who have defied gender norms, or read 7 Reasons Why More Men Should Wear Skirts
  • Most of all, surround yourself with open-minded and accepting humans

My partner provides endless encouragement and advice. She helps me see societal lenses and process whatever comes up. She's gifted hand-me-downs and much needed accessories like tights and earrings. We even have matching dresses. I'm lucky to have incredibly supportive friends as well.

I could never go back. There are too many things I adore about skirts and fem expression:

  • Less limitations (and being able to share clothes with my partner)
  • Compliments and inspired epiphanies from friends and strangers
  • Helping to dismantle patriarchal and hyper masculine ideals
  • Freedom, authenticity, creativity, and self-expression

Life is short and I want to avoid the #1 dying regret, 'I wish I'd had the courage to live a life true to myself, not the life others expected of me' (article + wikipedia).

Gif of me twirling in my first skirt (long, flowy, paisley orange/red/black/cream/blue pattern), with brown leather vest and brown tights.

This article was originally published on Medium in January, 2022.

Tags: People Story

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Thanks for sharing your experience, and your blog, Joey. It’s so important to find what works for our personal styles, and avoid any ‘shoulds’ around skirt types, colours, etc. The in-public anxiety definitely fades! And I think people are generally desensitizing.


Hello, I relate to so much of your story. I am a guy who sometimes wears womenswear as a man. Normally skirts and dresses. I have navigated toward wearing things that are not girly or feminine, but also not butch. Basically, I wear colors and patterns in women’s fashions that are not unlike what I am comfortable wearing in menswear. I found that I feel more well dressed in pencil skirts than flowy skirts. I’m finding my way… Mostly, my “dressing pretty” is still a secret. However, I go out in public with a LOT less anxiety than I used to. I’ve had quite a few experiences in public. Basically, a guy in a skirt is like someone with lots of tattoos, a wheelchair bound person, or someone with an exotic hair style or color. We are different. People might look. (Different people groups are more friendly or engaging than others.) Then nothing different happens after that. At least, that’s how it has played out in my town, with my personality, and with my choices… I blog about my experiences on



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