How (and why) to Wear a Skirt (as a man)

Right now I’m on a train headed to Toronto, and I will be on another train coming back, late tomorrow evening. I’ll be participating in a photoshoot at Ryerson University as part of a research project on men’s fashion. The focus of the study is men of my generation who are using fashion to express themselves, and changing what “masculinity” means in the process. I am expressing myself right now, with my fashion. It feels awesome, empowering, and graceful to wear this skirt.

I didn’t always wear skirts. I don’t always wear skirts. The vast majority of this year, my legs have been surrounded by inflexible tubes of fabric ready to tear in the crotch at the first full squat. This is how I got started wearing them, stopped, and started again.

At the beginning of 2015, I was not myself. I was “Travis”, yes. But I had little inkling of a soul, and no idea that I could be hiding feelings from myself. I ought to know what I’m feeling, right? Ours is an unfortunate society where many people cannot identify this feelingless feeling.

It began to change gradually when I was exposed to people who had the spiritual bent. They helped me look inside. I began experiencing myself on levels unknown for perhaps my early childhood. I realised eventually I needed to end the relationship which I paradoxically kept to dull my emotions. In June, it happened. I had shed the final vestiges of my heart’s steel armour – and I was ready to experiment.

Two weeks after this break-up, I left for Toronto, where I would stay for 3 weeks. I was performing in a rock opera aptly called “Johnny Legdick, A Rock Opera.” I played a pantsless half-horse named Steve the Steed. We had done the show three times before, in increasingly awesome venues in Montreal, and were ready to hit the Toronto Fringe. I took a Megabus with two of my colleagues.

Not one hour over the Quebec/Ontario border, the bus crashed. It clipped a truck and careened into the ditch where it was “gently” slowed to a stop by the treeline. I came out of it with little but whiplash and some traumatic images.

I view this event symbolically. The old, self-repressed, scared-of-his-emotions Travis was the only casualty of that event. I emerged, both stronger and more sensitive.

When we finally arrived in Toronto the next day, we had to find new clothes. Our luggage was being kept by police for two weeks. So, I set out to build a whole new wardrobe. I have recently become conscious of where I buy my clothes. I refuse to support companies that outsource production to sweat shops. So, we went to Value Village, and other vintage shops. (I also bought a pair of brown jeans hand-made in California, at the opposite end of that spectrum.) And I was determined my new wardrobe would include skirts.

I had always admired the wearing of skirts. “It must feel so free!” I would think, and every Scotsman would reply, “Well, duh!” I wanted to be graceful and elegant. I didn’t want to always be “the man”. I had been determined to find ankle-length flowy skirts. My legs being absurdly long, I settled for a calf-length flowy red skirt, and a knee-length green, um, pencil skirt? I don’t know, it’s just a tube with an elastic waistband.

Wearing them in Toronto felt awesome. I was exhibiting this new me. Everyone in the cast of Legdick (and in the bizarro world of the Fringe community) was super supportive. I did get some looks but that was part of the fun. I was spotted by a researcher for Ryerson wearing one, and got recruited for this photoshoot. I felt super vindicated.

When I returned to Montreal, I showed my new wardrobe to some specific, influential females in my life. I was incensed when they had constructive criticism. No such criticism existed in Toronto! I became aware that I didn’t know how to wear a skirt. I didn’t have the right shirts, or shoes. I started getting self-conscious. I bought a third skirt because it looked perfect (the one I’m wearing now! Brown and black skirt that buttons down the whole way). I wore it once outside, and after that, I stopped wearing skirts for months. Until today, in fact.

I felt so anxious walking down the street in that thing. I was afraid everyone was judging me. Either my outfit was dumb, or just the fact that it’s a guy wearing a skirt… I couldn’t relax. And what was worse, I was trying the whole time not to be anxious. I think we all know what that feels like. I suddenly developed this icky feeling for this skirt and by extension all skirts, and hey it was getting to be Fall anyway, so I might as well just retire them for the year.

But fall means fall fashion! I took a trip to value village and added some key items to my wardrobe. Nicer shirts, some boss ties, and at Eva B I bought a couple of chic vests. I started making snazzypants outfits and dressing in a hodge-podge three-piece suit on any old occasion. “Why are you so dressed up?” people would ask. That’s just who I am now. A guy who dresses nice for no reason, just for fun. Because it makes me feel good.

I know what you’re thinking. This wouldn’t be The True Life Story of a Pioneer without a little Maxwell Maltz, right? =)

Earlier this week, I read a chapter of Psycho-Cybernetics entitled “That Winning Feeling.” Before we continue, I want you to do a little exercise for me. When you finish reading this paragraph, close your eyes and imagine a moment in your life where you felt awesome. You were challenged, and you overcame that challenge, and you felt worthy.

Got it?

If it doesn’t come easily, try again. Go into vivid details. What were you wearing? What sort of sounds did you hear? Was anyone else there? And get in touch with that “That Winning Feeling.”

I can’t explain it any better than this, really. It’s just that feeling you get when things are going awesome – specifically, in a crisis situation. Crisis situation, here, refers to any situation where there’s a risk of failure and a reward for success. Public speaking, a darts competition, any video game, telling someone you love them…. In such situations, you have two paths: get anxious and freak out and probably fail, or stay cool, feel awesome, and probably win. Even if you don’t win, at least you failed and felt cool and awesome. If you could harness that feeling, call upon it at will, wouldn’t life be smoother?

Let’s say you’re a ten year old girl playing the violin. You are about to play your first recital. There are going to be like fifty people there! It’s easy to play on your own; if you screw up in your room no one cares. But now everyone will hear every mistake. The stakes are high!

Of course, the fear is unfounded. You are just as capable of playing on a stage in front of an audience as in your room. But distractions – like people watching – makes it harder to concentrate, and thus to get “That Winning Feeling”.

Our body-machines function by reacting to external impulses. The first time we experience a new impulse, we form new neural pathways which dictate how we deal with the situation. This is how muscle memory works. The mind thinks, “It’s time to play Frère Jacques,” and the body knows what to do because it’s played the piece a hundred times. The pathways are there, it’s pretty much a highway at this point, so it goes for it. No need for thoughts. Thoughts get in the way. But when you add a new impulse, the audience, suddenly it’s a whole new experience.

Meditation is focusing absolutely on one thing, material or abstract, without thinking. Just comprehending it on a spiritual level. Thoughts will always pop up, of course. It is the mistake of newbie meditators to believe we should be able to immediately dive into a trance and change our life in half an hour of sitting and closing our eyes. We must, over and over, develop the reflex to let the thoughts pass through, without provoking new thoughts. It is difficult and requires daily practice for many years.

I have a hunch that “That Winning Feeling” is the term Maxwell Maltz used to describe “Flow,” which Mihaly Csikszentmihalyi describes in more detail. Tl;dr: “Flow” is when you’re so involved in an activity you lose sense of time, identity, disconnect from reality, you’re just IN IT. In the ZONE. You know what I mean.

Meditation is the purest and most difficult flow activity. The aim in meditation is to achieve flow when there is no activity. Other activities, where you’re actually doing something, can induce a flow state much more easily. But the same principle of dismissing thoughts applies.

If you, as the 10 year old violinist, had already meditated every day since she was 5, it might not be so tough. She would be able to recognise the invasive thoughts (doubts) as what they are and dismiss them, and just give a great performance without fear. This is unlikely, however. Most of us are not gurus. There is, thankfully, a faster way to overcome the pressures that a crisis situation can impose.

We can acclimatise our bodies to stressful situations, much like diving. The key is gradualness. If you dive too deep too quick, your lungs will implode. Before performing for fifty people, do a private performance for your sister. She’s already seen the worst in you, so no harm in screwing up. Then add your parents. Then a couple of friends. Already, just by practicing in a low-stress, zero-risk, setting, the idea of performing in front of people is less daunting. You begin to open to the idea that it’s not the end of the world if you make a little mistake. But it’s still not fifty people, I mean come on.

The next step is to visualise. Recall once more that pleasant memory from before. That is an image – in the “imagination” sense of the word. It’s a “slice” of imagination. The great thing about being human is we can create our own “slice” that have never existed. Use the same technique of remembering to “remember” an upcoming crisis event. Look at yourself from the outside performing admirably, with poise, undisturbed – even unaware – of onlookers. Go into the same detail as in the memory. Conjure up that feeling once again. You are actively creating pathways in preparation for the real thing. The brain can’t tell between a real experience and a vividly imagined one. So it is possible, and desirable, to trick the brain into knowing that we’ve already done this before and it’s easy and feels awesome.

My “lungs imploded” when I went down the street in that skirt. I put too much importance on it. I chalked it down as a failed experiment and dropped the whole project. My mistake was jumping into the “fashionable person” identity with skirts before developing actual fashion sense. So I acclimatised myself by being comfortable standing out – looking dapper often and publicly. Now I better equipped, both with fashion and self-awareness.

I spent five minutes this morning picturing myself walking down the street, waiting for the bus, sitting on the train, in my skirt, and feeling awesome. People looked and I knew they were looking. I even imagined myself forgetting about what I was wearing. They’re just clothes. I’m not constantly thinking about the pants I wear.

I have felt awesome about wearing this skirt all day. And tomorrow, I will feel awesome in front of the camera. And I won’t focus on my clothes, but on my action – for photography is not about what the photo looks like, but what is happening in it.

Don’t be afraid to put yourself in a “crisis situation.” Prepare yourself, and there is nothing you can’t do.

Thanks for reading. You’re the best. =]

-T

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7 thoughts on “How (and why) to Wear a Skirt (as a man)

  1. Great stuff, Travis! I’m going to tag a couple of people I know who are about to do auditions; talk about crisis situations! xoxo Have great fun tomorrow at that shoot!

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  2. That’s a great article, Travis — well done. You hit a LOT of high points in there, and readers would do well to not just scan but actually digest some of them.

    Being a bloke who quite frequently wears skirts myself — and who has experienced more than a few times the power of “flow” — I can state that it’s all about confidence and comfort. It’s about confidence because people, like dogs, can smell fear and about comfort because if you’re not comfortable (in all its meanings) you won’t be confident.

    It took forty years to gain the confidence and comfort to put a skirt on and venture into the world. I wish I’d tried to gain that sooner. You’re never too old, but you can’t start soon enough.

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    1. Hey Carl,

      Thanks a lot for posting! Your experience is inspiring!

      Do you have harsh winters where you are? Do you wear skirts in the winter? I only have one that could potentially keep me warm enough….

      Best,
      -Travis

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      1. I believe you’ll find that there are more men “out there” who wear skirts than you might think at first blush. That said, it’s pretty rare to see more than one at any given place at any given time. The world needs more of us.

        I’m a “few miles” south of Montreal in central Massachusetts, so I can get some reasonably nasty winter weather, and for that I have long heavy skirts with underskirts (petticoats, actually — there, I’ve gone and said it) which make for a comfortable experience down to about -10 F. If it gets much colder than that I’m likely to take the approach of staying inside. Interestingly, a long skirt can be quite a bit warmer than trousers in the cold; the prime tricks are keeping the hem dry and from gulping cold air.

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  3. Fascinating and very useful post. I have rarely, (maybe never?) experienced that winning feeling before this year, which was the year I started wearing skirts publicly. First time at work was an eye opener for my personal feelings. Your comments hit the nail on the head, unfortunately that includes the ones about learning a sense of fashion. This Sunday I took the look up a notch at the Christmas party, and overall I’m happy with how it went, but disappointed I didn’t spend more time getting *all* the details right. Still well received and a good time though. Now looking for some fun accessories to go with the look. Keep on rocking the skirts!

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    1. Hey there partlyscot,

      I’m glad you liked my post. Accessories are key! Watches, satchels, belts…. I have a couple of necklaces as well, with crystals on (simple but effective).

      Congrats on the Christmas party. It sounds like a step in the right direction for you =]

      As for “That Winning Feeling” – as the great Joseph Campbell says, Follow your bliss! There you will find your true self, with all the pleasures and pain of self-expression. Life sure is a wild ride….

      -T

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