Me in a dress! And a skirt!

So a few days ago I watched the excellent tv adaptation of The Boy in the Dress, and it ignited a spark of curiosity in me. I’ve never thought about wearing a dress before; some people seem to consider my style somewhat effeminate (I have something of a passion for floral print), but everything I wear is “male” clothing. Despite regularly observing how much more interesting female clothing is (I see enough of it, working in a clothes shop), in terms of having much greater diversity in design, and use of interesting patterns and colour, it was always sectioned off in a forbidden zone in my mind. Until The Boy in the Dress posed the question: Why shouldn’t a boy wear a dress? What harm would it do?

So the next visit to that shop I work in allowed me to experiment. And gosh darn it dresses are pretty comfortable! That is to say, really comfortable! One single piece of clothing that does the work of an entire outfit, with no pesky fabric wrapping around your legs, amazing!

I also gave a skirt a whirl too, which has the same not-being-trousers advantages.

I tired on a few in fact, and generally found I did not like the strappier ones, or ones with low necklines. These are obviously designed to emphasis boobs, and as I don’t have any I thought they just looked ridiculous on me. Plus it just generally left me feeling exposed; while I love to be naked, I’m the other extreme when clothed; if I must be dressed I’m in long sleeves and trousers, hardly any flesh to be seen. Which basically lead me to dressing up a bit like a Roman, in a tunic, which men and women alike would have adorned back in the day. Isn’t fashion and history a funny thing?

I feel like if I did ever want to try it out “in the real world” I could “get away” with a skirt more easily than a dress. One is switching out from trousers, the other is entirely adopting the mode of womanness - Whatever that means, when on earth did we decide certain types of clothing are only suitable for one gender?

I’m not sure if I’d ever feel comfortable enough trying out such a look in public (he says posting photos on the internet). Even though I am very confident and secure in my identity, in all its aspects, such a protestation at gender norms is pushing it even for me. Wearing womens clothing is such a loaded statement. Can a straight male do so and withstand social demands and assumptions?

What do you think about a man in a dress, or a skirt?