A Bowler Hat Makes You Look Like A Circumcised Penis, And Other Style Tips You Won't Find In GQS

GQ's resident style expert Glenn O'Brien gets some rather interesting questions every month from his readers. So we thought we would have our own Drew Magary (who is also a freelance contributor to GQ) answer some of those questions himself. All questions submitted to GQ's Style Guy are anonymous, but we have been assured that they are real.

I recently inherited some incredible hats from my grandfather, including a very high-end, very well-kept brown bowler that I would love to be able to wear... Is there a way to integrate a bowler hat into my wardrobe without looking like an ersatz Hercule Poirot, the mustachioed Agatha Christie detective?

That's all your grandfather left you? A bunch of hats? And you find that "incredible?" That's bullshit. If my grandpa left me a bunch of smelly old man hats, I'd dig up his corpse just so I could kill him again. Quit being amazed over a goddamn hat. And quit using phrases like "an ersatz Hercule Poirot." It's clear that you're already straining to impress other people. A bowler hat will make you look like a circumcised penis. If I saw a guy in a bowler hat walking down the street, I'd club him to death with an even larger, heavier hat. Here are the list of acceptable hats for men:

1. Baseball hat

2. Winter hat

That's the list.

I recently noticed some of the Canadian hockey coaches behind the bench of NHL games wearing red flowers in their buttonholes. I gather it is for some holiday. Is it acceptable to wear a flower in the buttonhole or lapel of my suit? Or is that reserved strictly for proms and weddings?

I don't know. Do you also possess a magical flying umbrella? You know what you should do: wear a flower in your suit AND wear a bowler hat. Nothing would scream I DONATE TO PUBLIC RADIO quite like that. Tool. Why would you aim to replicate the stylings of an NHL coach?

I'm interested in buying a pair of Peter Werth brogues in green suede. They look cool, but how could I go about wearing them with a suit? Does the belt still have to match the shoes? Does dark green work only with certain suit colors? If so, what are they?

What the fuck are brogues? Who is Peter Werth? Were you born inside a Whit Stillman movie?

I'm a Johnny Depp-style fanatic for worn, distressed, patched, and repaired jeans. But where is the line?

You've already crossed it. "Hey guys, you know what really revs my engine? Denim that's had, like, shit done to it!"

I recently bought a sleek stainless-steel pen simply because it was the same one James Bond used in GoldenEye. Then a female co-worker mentioned it was "girlie." Is there such a thing as a girlie pen if it isn't pink or covered in faux fur?

Who buys a pen for themselves? It's a pen. You're going to lose it. The only reason to buy a fancy pen is if you need to get a shitty graduation gift for someone else. Buy a pack of Paper Mates. Then you can tuck one into your lapel. WOULDN'T THAT LOOK DANDY?!

Is it appropriate to tip your tailor? If so, how much?

Who has tailors? Everyone who writes into this column has pens and tailors and old hats... I think every single one of these questions was actually ghost-written by Tom Wolfe. "Is it OK to wear my captain's jacket to brunch? How many pairs of chaps is too many? What goes with this paisley saddle I bought?" I went to a tailor once at a mall and I tipped him jack shit. I don't remember him giving me a free handie when it was inseam-measuring time.

What kind of scarf would you suggest to wear with a black leather jacket? Nothing seems to match.

How much money do you people have? I can barely afford to buy brand-name socks. We are in a RECESSION, people. Apparently, these guys live in some kind of alternate universe where men have endless amounts to spend on bomber jackets and suede brogues and leather eye masks and whatever the fuck else they're asking about. I hate them. I hope they lose all their money in fedora futures and are condemned to a life of wearing nothing but American Eagles Outfitters apparel.