Well, before I go into TL:DR land, which it appears is inevitable, I will summarize it to the very boring and obvious answer of; I dress like this because I like to.
To clarify that statement, I have always liked to. I have always liked ties, bow-ties, cravats, waistcoats, brogues, spats, dress shirts, tuxedos and suits of every description, except skirt-suits. Not that I dislike them on other people, and I am generally of the opinion that everyone else in the world looks better in any set of clothes than I do, but I’ve never felt comfortable wearing a skirt. At both of the schools I attended uniform was compulsory. At Grammar school girls had to wear a skirt. Primary school was, initially, the same, but after voicing my preferences to my parents, and a discussion with our very wonderful headmistress, trousers were also permitted for girls.
I was the only girl in my class who wore trousers.
Did I find it embarrassing? No. Did I find that I could do cartwheels and hang upside-down on the climbing frame and run around in windy weather without being embarrassed? Yes. Was my basis for wanting to wear trousers simply practical? I’m not sure. At the time I suppose it was the largest reason, so it was the one I used to argue my case, but I had always hated wearing dresses and having people tie up my hair and generally attempt to make me look ‘pretty’. I was never a 'girly’ girl. I hated the colour pink, played with snails in the back garden and had an action man. I don’t think I thought less of people who liked Barbies and ponies, in fact I loved horses more than anyone else I knew- but I wasn’t into that realm. I liked horses and going riding because it was exciting, and I constantly read about Dirk Turpin, Robin Hood and King Arthur.
I liked adventure stories. Who were the people that I looked up to the most in those stories? Men. I am not saying that there weren’t female protagonists out there, or no female characters that I liked, but they usually didn’t interest me; they didn’t live lives that I wanted to live. There are more these days who would appeal to me, increasingly so, but we are talking about what was, and the fact was that associated with the male characters, and that if I ever grew up I didn’t want to be a lady, I wanted to be a gentleman.
I still don’t see anything particularly wrong with it as an aspiration, and I’m certainly not a grown up yet, so, I play at being one. I make believe, as all children are wont to do, visually as well as personally. Wearing bow-ties and tweed jackets makes people smile, and I like that sort of look anyway, but secretly (or not so secretly after this) I really just want to be a gentleman towards people. It’s my costume, yes, but it’s also a way of living.
Life is play. My wardrobe is my dressing-up box, the world is my playground, the gentleman is my character, and that’s fine; because no matter how other people put it that’s exactly how life is for them too. I just make it clear that I’m playing because I have so much fun.