How did working at Paul Smith influence The Impossible Cool?
I always liked the aesthetic of the ‘50s, ‘60s, and ‘70s. I had an uncle that was Bruce Springsteen's tour manager back in the day. I was always rifling through his photos of The Allman Brothers and whoever Springsteen was playing with. I always liked that stuff. My great-grandfather was involved with Kennedy so I used to see family photos of that too. I loved the stories being told by these older photos. Over the years, I collected them and put them into a folder on my laptop. 

When I was working at Paul Smith, there was this huge board in the  suit room—it was like analog Pinterest. The suit room there isn’t Savile Row, it’s a bunch of misfits that hang out in expensive suits. I worked with this guy named Clyde. He's a movie buff, so we’d talk about film, and we would post people up on this board. Men like Serge Gainsbourg, McQueen, Newman—people that are now up on my website. It wasn’t an inspiration board, we would just throw up pictures of these guys as homage. That, combined with already having these photos on my computer, led to the Tumblr. I thought no site out there was paying proper respect to these people who'd been setting the trends that were currently glorified by the Internet. Menswear was gaining steam at the time, but everybody was looking at was happening now, and not back then. I’m not the only one who did this, but there wasn’t really a concrete site that looked back and said “These guys did it before everybody, and they looked really fucking cool doing it.”

With Tumblr’s image-heavy format, do you think it’s easy for a lot of people to lose the context of what they’re seeing?
Oh yeah, definitely. It waters down some images that are very powerful. One thing that’s rough with Tumblr is it’s really easy for people that maybe shouldn’t have a voice to spread misinformation. That’s why my site looks the way it does. I never wanted to offer an opinion because I feel like it’s unnecessary for what I want to do. It’s just the last name and that’s it: Here’s this person, and this is who they are.

Where did the name come from?
Honestly, I was in my apartment in California on a Sunday, just messing around on the Internet and I just kind of made up the name. That’s when I started the website. It didn’t come from anywhere. I just made it up. It came from thinking that no one right now is doing it as good as those guys back then. That’s just the world it was. It’s not that people don’t have the same sense of style—the world was a different place. That’s where the “impossible” part comes from: We can’t go back to that.

Do you think it’s taken on a second meaning? After all, you’re posting photos of guys like Miles Davis and Paul Newman.
Yes, but I never wanted it to be like “you have to be an actor to be cool.” Ken Kesey and Jackson Pollock are just regular-looking dudes, but they’re just as cool to me as Paul Newman. I always wanted to convey the spirit that you don’t have to do a certain thing or make a certain amount of money to be “cool.”

 

If you have any sort of blinking on your site, music, annoying things like that—you are officially in the wasteland of Tumblr.

 

There was actually a kid who wrote a term paper on the site. He was the first one who got exactly what I was trying to say: Coolness is not a job, it’s not what you do, it’s not what you own, it’s not how much money you have. That point was very important for me to stress as the site began to get popular.

When did you notice that your Tumblr was gaining popularity?
I’m good friends with Michael Williams of A Continuous Lean. Williams gave it a shout on ACL, and I have to give him props for getting it out there. As soon as he mentioned it, it was off to the races, traffic-wise. 

Did it open up doors for you? 
It helped in a major way. Before, I'd worked with Michael on stuff for Cole Haan and did some things for Todd Selby, but I mean—I’m currently sitting on the side of the road on the PCH in California on a job for a major luxury brand. There are a hundred photographers out there, but Ghurka came to me because of my site. As much as the word “blogger” is overused and thrown around, the site definitely helped me with my career. It put me in front of a lot of people.

Do you think it gave you social leverage or credibility?
Yeah, and if someone knew I did that site, it was always easier to talk to them. I was in that menswear world a little bit, hanging out with Michael before the site came out, but as an observer. It was about a year or two before I launched the site. When it came around, people dug it, and it definitely opened doors.

What is your most reblogged post on The Impossible Cool?
It’s a Clint Eastwood picture and I think it has a little over 10,000 notes.

How many followers you have right now? 
I have 70,000 on Impossible Cool. I have 17,000 on A Conversation On Cool.

How many of the people who follow you skew into that younger demographic?
Tumblr is a younger generation. I’m 34 now. I don’t think there’s a ton of 34-year-old guys starting new Tumblrs. I noticed that youth is a huge part of Tumblr. If you go to the Popular page at any point there’s like cupcakes with sprinkles and kittens on it. I’ve always been conscious of what I’m putting out there, that coolness isn’t how handsome or hot you are—Frida Kahlo is on there as well as Jackie O. I wanted to show kids it’s not a comparison or contest.

So is Tumblr a primarily young platform? Ten years ago teenagers had LiveJournal and Xanga. Are they on Tumblr now?
Oh yeah, for sure. Now it seems to me that Tumblr is almost a standard. I would say it’s one of the first platforms that has had that status. I’ve never had a company come to me and say “Can you do a Blogspot for us?” or something like that. Kids are always the first ones to catch onto these things, and they’re always going to be the driving force behind this stuff. Youth has that sensibility to it. I think that the fact that it’s so popular with the younger generation is why Tumblr just sold for 1 billion dollars to Yahoo!

Do you think the popularity of The Impossible Cool is a testament to classic men’s style?
I feel like I can’t really answer that question. That’s sort of an ego question. I think people juust weren’t seeing these types of images. Getty wasn’t doing anything with their photos. Corbis wasn’t doing anything with their photos. When all this stuff started hitting the Internet, and people were seeing Steve McQueen looking cooler than anyone in the present day, I think that everybody woke up a little bit and went “oh wow, we need to look back on this stuff.” To me, before the Internet blew up the past, everybody was looking forward. Now if you flip through the pages of any magazine, everybody’s looking back. 

Do you think it’s a good or bad thing to sort of model your style after these famous icons?
It’s definitely a good thing because fashion—and I’ll use the word “fashion” because I don’t want to say style—within the past ten years has gotten a little ridiculous. I think it’s good for people to look back and notice that simplicity at its best will always win. To have a guy say, “I don’t need a striped suit, polka dot tie, and paisley socks to stand out; I can put on a black suit, white shirt, black tie, and look cool as fuck,” is a very good thing. I think people get a little bit out of control at times in order to get noticed.

Yeah, everybody wants to be a Nick Wooster.
Exactly, and not everybody can be Nick Wooster. Nick dresses crazy, and he’s one of the only people who can pull that off. There are a lot of guys who can’t go to a store, pick out a tie, and put it together with a shirt. The way these guys were dressing back in the ‘60s was an easy way to dress. They didn’t have crazy patterns, but they were making statements.

If you look at a picture of Mick Jagger, he looks cool in anything he has on. I remember this photo of him in a suit that was pretty ill fitting, but Mick still carried it very, very well. Any guy can look at that and see that it’s more about how you conduct yourself and put everything together, than about having the latest Junya Watanabe shirt.

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