On Randomness, Individuality, and the Spontaneous Image: My Interview with Amy Creyer of Chicago Street Style

Amy Creyer's Chicago Street Style is one of Chicago's best known style blogs and one of the most buzzed about street style blogs anywhere. Creyer's work has been featured in The New Yorker, Chicago Tribune, and Complex Magazine, among many other places. She regularly contributes to Refinery29, and is frequently among the day's top ten posts on Street Style News. She also holds down a full-time job as a copywriter for a major drug store chain. She is, needless to say, a busy woman, and it took a while to get the following email interview together. Here it is:

Brent:  How much of your time does blogging take up, and how do you balance paid work and blogging? Is your new job complicating your blogging schedule?

Amy: Blogging takes up no less than 20 hours a week, at the minimum. Yes, my new job is making it more difficult to find time to street-style hunt, but I always worked on my site & social media in the evenings so that aspect hasn’t changed.

Amy Creyer, posing for her new Chictopia page. Image by Amy Creyer 

Brent: Would you consider blogging a hobby? A professional activity? Something in between? Or something else besides?

Amy: I think blogging is just the medium for different types of creativity, with styling and photography being the two big ones. Fashion bloggers tend to either be stylists, using themselves as the “client” or “model,” or photographers. Those two divisions are typically referred to as personal style bloggers & street style bloggers.

Brent: You mentioned in your email to me that you are completing your thesis. Are you doing a Master’s degree? If so, in what? Does blogging have anything to do with your long-term career goals?

Amy: I earned a master’s degree in management. My blog is directly responsible for putting me in the position to start a career in advertising. It’s like I created an internship for myself and tailor-made it to my interests.

Image by Amy Creyer

Brent: What got you into street style blogging in the first place?

Amy: I always loved cities and people watching in cities. I spent my childhood in Manhattan so people-watching was a big part of my day-to-day life, and forms a lot of my earliest memories. I guess you could say I’ve been training my whole life.

Brent: What is it that keeps you doing it?

Amy: I enjoy the photography, I enjoy scouting for people to photograph, and I enjoy blogging. I love the entire process.

Brent: What do you look for in the people you take pictures of?

Amy: It’s different for each person. There has to be something about them that interests me, I’m not looking for cookie-cutter beauty or style.

Image by Amy Creyer

Brent: How long, on average, does it take you to find people to take pictures of?

Amy: It varies so wildly that I couldn’t even generalize or average it. Sometimes I see people immediately when I get off the train, other times I waste hours and go home without any useable photos.

Brent: How long, once you see someone, does it take you to assess whether you want to take pictures of them?

Amy: It’s instant.

Image by Amy Creyer

Brent: What’s your approach? What do you say to people when you go up to them?

Amy: What I say to people when I approach them changes for every single person and photo. There is no formula.

Brent: Do you tend to take pictures of people where you find them or find better settings once you do?

Amy: I take people’s photos where I find them, although sometimes I walk to the end of the block with them to find better lighting. I’ve never taken anyone farther than the end of the block where I found them. Remember, these are random encounters and all these people are on their way somewhere, we don’t have time to waste!

Brent: Do you ever make appointments with people to take their picture?

Amy: My street-style photos are never scheduled. From time to time I’ll do an in-depth post on another blogger, but I’ll always put at the beginning of the post that it’s a special feature and was scheduled. Honesty is very important to me. A lot of street-style photographers schedule their photos, but I don’t think that’s real street-style.

Image by Amy Creyer

Brent: How spontaneous do you think street style photos ought to be? Does it matter?

Amy: If it’s not spontaneous it’s not street-style. That’s a fact. Pure street-style has to be random, because the entire magic of the art is documenting the way people dress for themselves and their everyday lives. The second the person dresses for the photoshoot the magic is gone.

Brent: How important is it that street style photos take place on the street?

Amy: It’s not street-style if it’s not on the street, sidewalk, park or outdoor public area. That’s the whole point, the setting is a critical component of the art form.

Image by Amy Creyer

Brent: Where in Chicago do you tend to shoot?

Amy: All over! Where ever I go shopping, run errands, work, go to class, etc. I always bring my camera because I never know what I’ll see.

Brent: What kinds of fashion events, both in and outside of Chicago do you attend? What do you get out of doing so?

Amy: I rarely attend public fashion events in Chicago anymore. I just don’t have enough time!

Brent: What do you think the impact of blogs have been on the fashion industry?

Amy: I think blogs have democratized fashion to a certain degree, but real influence is restricted to an elite group of bloggers who wield an enormous amount of power. Blogs have made fashion more interactive, which is great for advertisers and brands because it means they have a greater opportunity to build relationships with consumers. I also think that bloggers have been instrumental in the individual style that arose in the 2000s and is still going strong.

Image by Amy Creyer

Brent: Do you think your photos have a particular aesthetic about them, and if so, how would you describe it?

Amy: Since they’re all taken by me, I would assume that my photos look similar but that’s just a reflection of my eye and how I shoot.

Brent: How would you describe the aesthetic of your blog as a whole? Does Chicago Street Style have a distinct visual brand?

Amy: I keep my brand simple, modern and elevated. The focus is on the photographs and the experience of these people

Brent: I know you’ve worked as a social media consultant. Do you have any advice for aspiring bloggers about using social media to promote their sites? Which social media platforms do you think pay off the most? Which are perhaps not worth one’s time?

Amy: There is no formula. The key to social media success is in trying out different platforms, finding what works best for you, and then working hard to communicate well.

Image by Amy Creyer

Brent: How important is it to you to have a lot of traffic to your site? Would you still blog if only a few people were reading what you post?

Amy: Traffic is not important to me. I blog because I genuinely love and enjoy the entire process of street-style blogging. I blog for myself. That’s why it’s so funny to me that my blog became so popular and has so many passionate readers, because it’s really just a labor of love.

Brent:What are your feelings about ads, sponsors, paid content, and the like? Do you have any personal policies you adhere to?

Amy: I think paid content, ads, and sponsors are great ways to enhance the blogging experiences as long as it’s a natural fit with the brand. I only agree to work with less than 10% of the companies who approach me for collaborations. It really has to be the right fit.

Image by Amy Creyer

Brent: To the best of your knowledge, what is the readership of Chicago Street Style like? What kinds of people read it?

Amy: 40% of my readers live in Chicagoland (Chicago & the suburbs). Only a miniscule proportion of my readers are other bloggers, less than 5%. I LOVE that about my readership because they’re people who truly enjoy the photography and the people watching aspect of it. People aren’t visiting my blog to leave superficial comments with links to their own blogs like you see on most popular blogs.

Brent: What blogs do you regularly read? Who are some of your favorite street style bloggers?

Amy: Mr. Newton and Tamu McPherson are two of my favorite street-style photographers, although Shoichi Aoki is my all-time favorite just because I discovered street-style through his work in FRUITS.

Brent: What advice would you give to someone looking to become a street style blogger?

Amy: Expect to work very, very hard if you want to do a good job. Street-style photography is very time consuming and can be emotionally taxing, but in the end is always extremely rewarding.