Esquire’s EJ Samson on Timberland, Instagram and the Future of Digital Journalism

EJCome hang out at our Chicago flagship store in Men’s Shoes this Thursday from 5-7PM, where we will be hosting special guest EJ Samson, director of content strategy for Hearst Media Group–aka the guy who runs the website for Esquire.

It should be fun. All the event info is here.

Samson put together outfits featuring Timberland boots which will be on display in the store. He will be ready to answer your questions.

Ask him about the outfits. Ask him about Esquire. Dance to the deejay or stomp around in your Timberlands and enjoy light bites and cocktails.

To get to know him better, we called Samson ahead of the event and asked him about his history with styling and his visions for the future of digital journalism.

Shop: Timberland

Nordstrom blogs: I know your professional history, a little–you work in publishing–but what’s your history as a stylist?

My background is as an editor for ten years. I started at Teen Vogue of all places, was the digital director there and then became the digital director at GQ. I’ve always had a love for fashion and putting outfits together. I feel fortunate to have been behind the scenes at those publications. I’m in awe of [Esquire fashion director] Nick Sullivan and the looks he puts together for the magazine. It really speaks to me, right now, how I get dressed for the day. But I started to hone that craft through Instagram. It’s an immediate litmus test. Commenters have no problem telling you, “That tie combo is not good. And I wouldn’t wear those jeans. Or those shoes.” Prejudgment on your style. It’s right there. But at the end of the day I dress for myself.

Screen Shot 2015-11-09 at 2.42.18 PMSamson’s actual feet on his actual desk

Shop: Johnston & Murphy shoes

So when people criticize your outfit on Instagram, it doesn’t hurt your feelings?

No, I like to consider it constructive criticism. It’s easy for people to have strong opinions behind their screens, but I try and peel away those layers and find the constructive notes that help me get dressed the next day.

You work in digital strategy. What is that?

I was an editor, creating content. Now, I’m still telling stories. But the stories are most of the time sponsored by an advertiser. Still telling stories, but adding a brand layer to the overall picture.

You’ve been on both sides of the editorial/advertising borderline. Is there any difference to you at this point?

I like to say a good story is a good story, whether or not it’s underwritten by an advertiser. On the publishing side, you get the KPIs and brand messaging from an advertiser, but you still have to flex that creative muscle and, in this case, see it through the Esquire lens. It’s my job to find that happy medium. I work at lot with Jonathan Evans, who’s the style editor of Advertisers come in wanting to advertise on our site, with something revolving around X, Y, Z themes. I’ll run that by Jonathan or another editor. And he won’t necessarily write the ad, but he will have thought about it from the Esquire point of view. I always work with the editors to make sure they’re on board. Consider the website an apartment complex. The editors are your landlords. We’re renting space on their property. They approve content like a landlord approves a tenant.

What’s the difference between that and social media stars who feature brands’ products in their selfies?

In my mind, there’s a difference between digital journalism, like Esquire, and social media. A celebrity Instagrammer maybe isn’t as forthcoming with whether or not their clothes were gifted to them or whether they were paid to post that picture. But Esquire, we’re extremely transparent about it. We say, We partnered with Timberland to tell you the top trends of fall that you need to know. On, if we do team up with an advertiser, the byline will say Esquire + Timberland. I’m happy with the way the industry’s going in digital. I think there’s a lot more liberty, where promotional branded content can live in the same places as editorial content. But we have ethics and practices. And one of our main values is transparency.

Glenn O’Brien is writing for Maxim now, which is big news in your world. Who are the other main competitors for Esquire?

The usual suspects: GQ, Details, Men’s Health. But frankly on the digital level we’re competing with BuzzFeed and even Thrillist. Digital pure plays take a big chunk of our traffic. I think you have to look at who’s killing it in digital, period. Not just who’s killing it in the men’s space.

Good point. What’s the next widespread user-facing innovation we’re going to see in digital publishing? Besides push alerts or customized news feeds. What’s next?

My personal opinion: there’s a lot of noise on the web right now. I think what we might start seeing are a lot cleaner user experiences, not a lot of moving pieces. There was a huge movement a few years ago, when The New York Times had that “Snowfall” article. Which was really cool. It was like a movie. But then everyone started copying it, adding animations, maps and GIFs to their pieces almost just for the sake of doing it. I think if it doesn’t need to be there, don’t do it. I think we’re heading toward a movement when the words and content will speak for themselves. Streamlined, minimal. And it will be a challenge for us on the publishing side to channel an advertiser’s content that way too.

To change gears almost entirely: What’s your mindset going into the event in Chicago, and how are you thinking about Timberland on the modern male in 2015-2016?

What I’m impressed with is, Timberland’s been a brand since I was a kid. You’d have those tan boots that you tucked your jeans into and had the tongues hanging out the front. I paired them with oversized Nautica polos. That was how I dressed when I was a kid. For a long time, that was my association with the brand. But looking now at everything that Timberland does, at all the product they have to offer, I’m really impressed with how they fit every guy’s style, whether you get suited up for the office every day or have a more casual sense of style. So next week in Nordstrom, I’ll definitely be speaking to the versatility of the brand, which I’m really excited about and impressed by.

–Andrew Matson

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