Somehow I discovered The Grumpy Owl before I knew that the writer, Ryan Oakley, was only one degree of social separation from me.  Now I count him among my friends and he is also a client – I did an illustration for his calling cards.

Ryan can be very agreeable if you disagree with him.  I sent him a few daffy questions in an email and he generously answered them.  Enjoy, and if you would like to be provoked further go read his blog.

Sometimes when I describe you I’m right (misanthropic) and sometimes, I’m wrong (contrarian). So, for those who don’t know you or The Grumpy Owl yet, how would you prefer to be described?

I prefer to be indescribable. Every description is always a mixture of accuracy and inaccuracy and it’s hard to say what’s worse. Whether right or wrong, a description of a human being too quickly becomes a subscription to a set of values.

It’s just a way of neatly packaging someone, usually for marketing purposes, and it denies the basic complexity of the human mind. Being too clearly defined is like being dead. Having said that: “Ryan Oakley what happens when Beau Brummel and Genghis Khan mix sperm to have Quasimoto’s love child via Ronnie Gardocki’s brain- womb.” Change the present tense to the past and it’s an epitaph.

You have a lot of fashion blogger friends and you are one of the only bloggers in Toronto with a strong view on menswear, though the range of your writing is far beyond the scope of fashion. What do you like about fashion blogging and fashion bloggers?

Some of my best friends are fashion bloggers. I just rode their coattails into it.

For some reason, a lot of my friends became involved in fashion at roughly the same time. Going out with them meant going out to fashion-related events. Going out to fashion events meant meeting more people who were involved with fashion. Some of these people I get along with, some I don’t. To me, most are just trees. They might look nice but I don’t want them in my living room.

As a subject, fashion goes to the heart of a lot of issues that interest me. It’s social, economic, artistic and poltical. And it’s hilarious when fashion tries to address these issues. Like watching a dog chase its tail.

Global warming, sweatshops, a solid bulk of the wars on this planet, directly relate to the spending habits of The Western World . Fashion forms those habits. Fashion *is* those habits. The only thing more shallow than a fashionable cause is to be uninterested in the causes of fashion.

Like cancer, we need to understand it if we’re ever going to cure it.

Can you recommend any favourite fashion blogs or websites, especially specific to men’s clothing?

My two favourite sites look done. Dandyism.net has declared itself in exile but might be dead. The London Lounge looks like it’s dead but might just be in exile. Hopefully both will be back. The London Lounge, in particular, was a great site. It counted the world’s best tailors, dressers and menswear writers amongst its ranks. There were always great illustrations, a lot of insight and a variety of opinion.

Most of what you read about menswear online was taken from there.

A Suitable Wardrobe is a regular read but I dislike how Will dresses. I say that with no malice and a great deal of respect. We just have wildly divergent philosophies. Even if he lacks the poetry, Will knows the grammar. If you want to know where a comma goes, he’s your fellow. He’s the Strunk and White of suits.

Simon Crompton’s blog, Permanent Style, is quite good and based around affordable options. Thomas Mahon offers a Saville Row tailor’s take on things at English Cut and I like Barima of Style Time. That fellow is genuinely innovative.

You share your opinions on The Grumpy Owl, your reviews on other websites (Mooney on Theatre, blogTO), and you also write fiction. For those who want to read Ryan Oakley’s fiction, where should they start? What kind of readers like your fiction?

My first love is fiction and I still have a few old irons in the publishing fire but I no longer submit.

I stopped submitting when I wrote a story with nothing but contempt for the intelligence of the reader, no original ideas and told the whole thing with a cynical formula. It sold to the first place I sent it to. I repeated the experiment a couple of months later and the same thing happened. Meanwhile, a book that I cared about and knew was good, was getting personal notes from publishers claiming it was good but too violent.

So fuck it. I gave up. If something falls in my lap then fine. Otherwise, I’ve already spent too much of my life chasing that dragon. If that dragon wants me, it can chase me. I’ve been staring at its asshole for too long and only have a suntan to show for it. I can’t be bothered with the heartache of coming close again. That shit hurts and life is too short.

Besides, it was never about the money or the recognition. So even the goals are dubious. It’s like courting a woman who’ll probably reject you and who you don’t even really want to sleep with. I just write the sort of books that I want to read but can’t find. Turns out that I’m a small audience. But a happy one.

I also write an irregular etiquette column for The Worldwide Culture Gonzo Squad Inc. I was promised no profit and complete freedom. I like that.

It seems like you do exactly what you want to do most of the time. Do you have any further ambitions or have you already perfected the art of being Ryan Oakley?

There’s only been one perfect man and his name was Burt. He lived in my friend’s basement. Raised monkeys and sold them at a loss to local Gaugins. Went out of business when the pox hit.

I’m not even sure what that means – to perfect the art of being Ryan Oakley. I have an idea of the man I’d like to be but I often fall short of that ideal. The one time I reached it, I was kicked in the mouth and knocked unconscious in the street. One day, I’ll get a gold tooth to commerate that.

As far as ambition goes, I have no need of grand schemes. It’s hard enough to deal correctly with what nature puts in your lap without adding an imagination to your problems. My only real ambition is to do what’s in front of me welll. It’s hard enough and I fail too often. But what the fuck? That’s life.

Put on one sock at a time and try again.