On the morning of November 27th, the Coach store on Michigan Avenue closed down to the public for an intimate breakfast with Chicago’s leading fashion media and Scott Schuman, The Sartorialist.

He was in town to celebrate his new book Closer, a deeper look at some of the street style images that have made his blog so famous. The Q&A was conducted by Susanna Negovan, editor of Sun-Times Splash and here are our favorite parts of the conversation.

You began at a time when street style blogging didn’t exist, in fact you pioneered it. So what was your inspiration behind doing it?
I think I would say to that, you know that I didn’t think that much ahead of time. I’m a very type A person. A: there was nothing to lose, there was no barrier to get through, it doesn’t cost any money to start a blog. I came up with what I thought was a very good name. I thought that was important because now you see so many people that do like Stockholm Street Style or Berlin Street Style and with that you know exactly what you’re going to get when you click on that button. I thought The Sartorialist was vague enough that when you went down the blogroll it would create a mystery about it. So I knew I had a good name. I knew I could probably get better at photography and learn how to shoot what I felt about fashion and make it very clear what I felt about that particular look or scenario.

What was the moment and how long did it take before you felt like, maybe I’m onto something?
I did sales and marketing for a long time, and I’ve had my own showroom, worked with Valentino and a lot of these companies and when you’re selling something you can tell them everything. You can’t make somebody love something. Right? They just have to love it. You can’t convince them or talk them into it. I was doing the blog for awhile and I’d just start getting these e-mails from people out of the blue saying: you’re blogging so much, I love the pictures. I love seeing people like me. I can relate to these photographs more than looking at fashion magazines. The fact that people were taking the time and e-mailing me these heartfelt sincere e-mails about what the site meant to them was great. That’s when you know you are onto something.

One of the things as an editor that I would like to know is just the mechanics of doing what you do. You wake up in the morning, do you go to a specific corner? How do you stop people? Do you style them?
It’s different when I’m on the road than when I’m at home. When I’m in New York, you have to do the business of getting ready for the next trips and all of that so I spend X amount of time working with employees and doing things like taking the kids to school. In the beginning I would go  out and walk around, a great part about the job. I thought it was very fascinating. It was such a romantic idea that your whole day you could just go out and walk around all day —walk around the city, walk over here, walk over there, by yourself. I thought that was pretty cool. Now I don’t walk so much.  I’m on a bike. I just get on my bike and go because you can’t make it happen, you have to put yourself in a position to find a photograph. Sometimes that shot doesn’t come until you say, okay, day is over and you’re on your way back home. That’s the real challenge to keep that energy level up all day or as long as you’re out.

When you approach people, is the answer always yes?
No. Especially when I try to challenge myself and travel more. We go obviously to Paris, London and Milan but in the last five weeks I’ve been to Posen, Poland (which is like their 5th biggest city), South Africa, South Korea and Tennessee. I’m not always asking fashion people, I’m asking whoever I find. I’ve gotten pretty good at reading people and seeing who I think will probably say yes.

Do you intend to do this for a long, long time? After a while do you lose interest in shooting people? Have you seen an evolution of style that keeps you captivated?
Have you heard something (laughs)? I wanted to be the next Armani when I was 14 and I’m not 14 now. So it’s a world I’ve always been interested in and the fact that we have a front row at Prada, the fashion element is only one part. I go through two worlds, the fashion world and the photography world. So when I get a little bit too much of the fashion world, I can work more on the photography element.

Photos by Barry Brecheisen: Jena Gambaccini (ChiCityFashion) and Scott Schuman (The Sartorialist); Corri McFadden, Erin Brennan, Bridget White (All from eDrop-Off);  Meg Mathis (Michigan Avenue Magazine), Carol Calacci (SecondCityStyle), Melissa Maynard (Factio Magazine); Suzanne Kopulous (Garmental), Anna Blessing, Emma Arnold; Jared Hatch (Racked) and guest; Scott Schuman and Susanna Negovan; Toni Canada and D. Graham Kostic (Glossed and Found)