Gawker Emily is not going to hell, but she may be going to the Reading Festival very soon - at least if her newfound curiosity in Trilby hats is to be believed.

Last week, she emailed us asking, “What’s up with the Pete Doherty hat?”

So began an odyssey that left us sitting in 7A, ticking fifteen Trilbies through the windows during Sunday brunch. We flipped through US Weekly and realized that Joel Madden, the Good Charlotte rocker, may be America’s foremost champion of the Trilby - aside from the tattoos, it’s the only thing he seems to wear constantly. And then there’s Pete Doherty, whose hat may as well be glued to his moppy hair, which somehow looks disgusting and amazing all at once.

Eventually obsessed with the Trilby, we sought Men’s Vogue’s elegantly wicked Stephen Watson, the happily terrifying Nick Sullivan of Esquire, and fashion oracle Josh Madden (who also styles Good Charlotte) for the expert take on the Trilby…

An antique photo of the Trilby hat, early 1900s

Nick Sullivan, Fashion Director, Esquire: “Because of central heating, we don’t need hats anymore - we stopped needing them in the ’60s, but men wore them 1) for convention and 2) because it was cool. But in the early ‘60s, Kennedy stopped wearing the hat, and then it turned. He’s been blamed for killing the hat. Now, the only reason to wear a hat is for people to look at you.

You see far more men wearing hats in New York than you do in London, far more. I was quite surprised, I’ve been here three years. The trouble with wearing that hat here is that people won’t think of Pete Doherty, they’ll think of Michael Jackson. That’s a good thing possibly - compared to Kevin Federline. It’s a “Look at me, I’m a rock and roller” idea. The biggest problem with hats is the people underneath them!â€?

Run DMC sports their Trilbies in the ’90s

Stephen Watson, Fashion Director, Men’s Vogue:

“More power to Pete Doherty for wearing a Trilby! It’s such a historical hat, and he’s taken a very traditional menswear staple and subverted it. That’s why it works. But unless you have Kate Moss on your arm, should you wear it? I would say no - not unless you’re a complete Dandy and going for it all the way.

I would advise a rock kid to avoid it because you’ll look like a Pete wannabe – let him own it. Hats in general, you really have to own your own look. We just photographed Christopher Buckley and he wanted to wear his hat. At first I was like, “Oh no, that’s not going to be great.” But it’s so organic and natural to who he is, so the pictures were fantastic. You just know when it’s the right hat for you.â€?

Joel Madden wears a Trilby with Dior Homme to Fashion Week

Josh Madden, rock stylist (via email):

“Mod/ Ska style is very alive, and I think the music is really showing up now, as the beloved Pete plays songs with exact riffs of well known ska tunes, Lily Allen covers “Blank Expressionâ€? live, and then Razorlight, Peter Bjorn and John, and Of Montreal have ska (I mean original ska) tempos to their songs…

All of the fashion comes back… When the kids start to make a fuss, this beat, whatever it is, comes back… It’s not running away on a coke fueled club song, it’s bobbing along facing the mess.”

Hedi Slimane plays with the look in Dior Homme’s shows… Karl Lagerfeld also toys with it for women this season…

For more information, Josh reccomends these hat sites:

http://www.millerhats.com/hatcare_index/hatfaces.html

http://www.hatsandthat.com/otherfeatures_trilbyhats.htm

And so we do, too.

PS:

Trilby is also a model from Brooklyn. There she is in the middle, next to the guy in… um… the Trilby.