Jesse Thorn didn’t set out to be a menswear authority—but through happy accidents and hard work, he finds himself as the main dude of Put This On, a video series and blog about “dressing like a grownup.” Jesse and the PTO crew, including directors Adam Lisagor and Ben Harrison, comedy-type-person Dave Hill, and blogger Derek Guy, have tackled topics like choosing denim, caring for shoes, and developing personal style. In the sometimes impenetrable realms of tailors and industry insiders, PTO’s content is refreshingly forthright and accessible. Rigorous research and respect for tradition inform the series and blog, but the content is leavened with recognition of the silliness of unchecked clothing nerdery. Constantly updating the PTO blog, Jesse and Derek amplify original voices in men’s clothing, and also give readers the heads up on choice sales or eBay auctions. They also write for Styleforum on occasion, and Put This On is sponsoring Styleforum’s 10-year anniversary event coming up May 4-5, 2012.

Put This On recently debuted episode 1 of its second season, and I talked with Jesse about how far PTO has come and where it’s headed this season.

Photo taken at Don Ville shoes by Gordon De Los Santos.

Pete Anderson: Put This On debuted with an episode on denim more than 2 years ago. Your first season had seven episodes of about 10 minutes each, plus some short followup videos, leading up to season two. And you have a Tumblr that’s on the dashboard of everyone seriously interested in men’s clothing. When you first started filming, how much of this was part of the plan?

Jesse Thorn: When we started, the plan was just to shoot one episode. The blog was just a way to engage the audience a bit before that episode came out, but it took off right away. To our surprise, frankly. We set a more ambitious fundraising goal for the rest of our first season, and met it handily, and while we were producing that, Adam was getting busier and busier with outside directing work. I was working on the blog to keep our audience engaged, and it was growing to the point where it was the most popular thing I was working on. At that point, the series and the blog felt like they were feeding each other.

My background is radio and television host, and I wanted to get some on-camera experience working on a subject that I really love, and one that really wouldn’t work in audio. I had a friend who was a brilliant director. Then we sort of discovered accidentally this audience for the blog.

PA: In a teaser for season two, PTO featured writer G. Bruce Boyer, who said in the piece “Real dressing is about understanding yourself and your clothing and the relationship between them.” I think that sums up pretty well what PTO aims for–how accurate is that?

JT: That’s very fair. Derek and I both have our own personal aesthetics, which we’ll give voice to on the blog, but we also both try to make clear that our goal is to encourage people to make thoughtful choices about how they present themselves in the world. Not just because they should always be the best-dressed guy, but because dressing well is a way to show respect to those around you, whatever your aesthetic or cultural context might be.

PA: I thought Jason Marshall (a Styleforum regular) expressed that very well in his piece in episode one, which also includes a segment on Lo-Heads with Dallas Penn, and one on Worth and Worth hats. Why did you choose the topics and interview subjects for season two? How much time did you spend with Penn and the Polo crew?

JT: Before the season started, we did a bracket on our site to find out what our audience thought were the three greatest men’s style cities in the world, and the winners were New York, London, and Milan. We didn’t think we could encapsulate those cities in 20 minutes apiece, so we decided to focus in on a few subjects for each one. In every episode, there’s one man, one place, one feature and one Q&A or how-it’s-made segment. We didn’t really think that we could perfectly represent some truth about the cities with those few segments, but we thought we could offer a few different ways of looking at each one, and tell some interesting stories.

In episode one, we were thinking about what’s really special about New York, and in larger part about the US. It’s a nation of immigrants, and a nation of subcultures, and we wanted to look at the ways that class, race, culture and identity intersect in a way that they only could in New York. I’ve written a little about why we chose the Lo Heads’ story to lead off the season, but in short, I think they’re recombining and reinterpreting the meanings of clothes at an extraordinarily high level. Jason’s a more traditional case—but he’s an elegant and eloquent guy who we met at a screening of O’Mast and were just struck by. Worth and Worth is another place that we liked because it got at that theme—what Orlando and company do there has a very sincere respect for tradition and a very sincere interest in creating something new. And, you know, we just threw Rob Corddry in there because he loves Put This On, and if you’re friends with Rob Corddry, you get him in your show, right? The next New York episode, I go thrifting with the guys from Street Etiquette – who are also StyleForum members – and we talk with Len Logsdail about what’s inside a suit, among other things.

PA: Looking forward to seeing that footage! Presumably you traveled a lot for season two—can you share any good stories about your globetrotting? What good stuff did you bring home, sartorially speaking?

JT: When we were at G. Lorenzi in Milan, I asked Sr. Lorenzi about which scissor I should use to trim my moustache, and he and his salesman guided me through a panoply of options. It was really remarkable. In the end, they wouldn’t let me pay, and I tried to force the issue for journalistic ethics reasons, but I could only go so far. So I took it and resolved to send him one of our pocket squares as a thank you in return. I put it in my dopp kit, which was in my carry-on bag… and when we left Milan, I had to check my other bag, which was big and had gear in it. And the moustache scissors set off the security X-ray (apparently no scissor is small enough to go on a plane these days) and I ended up having to pay a $75 baggage fee to keep the scissors Sr. Lorenzi so kindly gave me for free. On the plus side, the security guard in Milan was exceptionally nice. He said to me, in Super Mario-like English, “These… these are-a very a-special-a scissor.” And I agreed.

PA: Put This On is sort of moonlighting for you, since your day job is hosting Bullseye (formerly the Sound of Young America) a long-running public radio show that focuses on conversations with cultural figures. Describing it that way is honest doesn’t do justice to the thoughtful, often funny, in-depth pieces Bullseye does with people who are genuinely doing original work in comedy, music, film, TV, writing, etc. Do PTO and Bullseye cross paths often? The Rob Corddry cameo in season two was amusing.

JT: Well, our interview with Paul Feig from last season is a good example of the two paths crossing. Paul has been a guest of mine on the radio several times—for his books, and for his first film. It was in the old days, when I did interviews by phone, but we were friendly via email. Then 2 or 3 years ago, Jenna Fischer came over to do an interview, and she said she thought it was sweet that I dressed nicely for work, and said Paul Feig wore a suit to the set every day. When we were thinking of ideas for the show, I remembered that about Paul, and emailed him. He got us special permission to visit the set of Bridesmaids and did that interview while he was on his lunch break. The only rule from the studio was that we couldn’t say the name of the film we were on. But it was exceptionally kind of Paul to finagle us into his schedule—and we still email about clothes nerd stuff. He just had his first Savile Row suits made.

Rob’s been a guest on my comedy podcast Jordan Jesse Go several times, and he was nice enough to invite me and my co-host Jordan to help with a table-read and punchup of a script he was working on a couple years ago at HBO. He loves clothes and I helped him get a tuxedo for The Comedy Awards once, so he recorded that bit for us. There are a couple of other LA comedy people who have PTO connections—when Donald Glover was on tour people kept sending me pictures of him in a PTO t-shirt. He’s obviously a very well-dressed guy. I keep thinking we’ll find a way to work my friend and colleague John Hodgman into an episode sometime. He wrote a great thing about dressing like a deranged millionaire in his new book that we excerpted. Many comedians I know still dress like total slobs, but a surprisingly large number are taking an interest, and some, like Don or Aziz Ansari, are genuinely well-dressed. And I’m always surprised at the people who’ll say something nice about PTO to me when we’re talking about showbiz stuff.

PA: Can you tease any of the upcoming episodes of season two?

JT: My colleague Ben got to spend a day with Luciano Barbera at the Carlo Barbera mill after I lost my passport and got stuck in Brooklyn. We shot some amazing stuff with Guy Hills, the founder of Dashing Tweeds, who is just a phenomenon of a man. And at W. Bill, on the other side of the tweed spectrum. We went to 10 Corso Como in Milan, which will probably be the fashion-iest thing we’ve ever done, but Milan is the world’s fashion capital, after all. The trip to G. Lorenzi that I alluded to nearly left me in tears I was so inspired. We met two men who identified themselves as dandy-artist-pornographers. It was quite an adventure.

PA: You’d said Adam was getting busier and I’m sure you have been to–is season three yet a possibility? How about PutThisOnCon?

JT: Ben Harrison has been doing an amazing job as director in season two, and Dave Hill is stepping into Adam’s on-camera roll in the Rudiments segments. Adam’s still an executive producer, he created the template, aesthetically, and he’s advising Ben, but at this point, it’s really me and Ben’s project. My schedule’s been getting tighter and tighter, but the good news is that our audience has paid us a reasonable wage to make these things, and has demonstrated a willingness to do so again. We’ll see how we’re feeling in a few months when season two wraps up, but I’m excited about the possibilities for more videos.

As for PTO-con—that’s a fun idea, but not one we’ve pursued. We’re really proud to be a sponsor of the upcoming 10th Anniversary of StyleForum. We’re going to show something before Gianluca’s film O’Mast, and I’ll be on-hand in person. A couple years ago at MaxFunCon, Will Boehlke did a great seminar on dressing for men, and I’ve thought about doing something like that myself some year. Frankly, I already do a show at MaxFunCon, and between that and logistics, adding a seminar might be a bit much, so maybe that’s a pipe dream, who knows? People have certainly asked me to, though.

PA: Thanks Jesse—see you in San Francisco.