Although I will admit I’m a a bit biased as a native Chicagoan, I’d like to think that Chicago is a very stylish city. And while there is a street style blog in virtually every major metropolitan city in the world, the MidWasteland captures the best street style photos that display Chicago’s style. I was very happy when I got the chance to interview Monica Dimperio, the face behind MidWasteland, to discuss her take on Chicago street style, where she takes her photos, and her recommendations on some great Chicago shops.

Tell me a bit about your background.
My fashion background consists of a degree in Media Management from Columbia and several years in retail. I worked as a manager and merchandiser at stores including: Lacoste, Prada, and Adriano Goldschmied.

What inspired you to start The MidWasteland?
I got into fashion blogs in early 2007 before a big trip to Europe. Facehunter and Stil In Berlin are two that I really liked. When I was there I saw the most amazing style. When I came back I saw things differently so I picked up my camera and started capturing Chicago street style in July 2007.

Why did you name the blog The MidWasteland?
It’s been a while so I can’t remember the process but I know that I wanted a name that let people know that this wasn’t a blog you wanted to take seriously, like The Sartorialist, for example. I wanted to create a place for people, like me, that know firsthand that most Midwestern stereotypes ARE true. Though, on the same token, also know that style exists within our region, which is why I think The MidWasteland fits nicely. We’re all about having fun here.

Where in Chicago do you take most of your street style photos?
When I first started in 2007 I mostly shot in Wicker Park because that’s where I lived and it was always easy to spot a stylish person there. Now I take my camera everywhere I go. There are stylish people all over the city so I can’t say just one neighborhood.

What Chicago neighborhoods do you think have the most style?
I’ve lived here my entire life. I find beauty in every neighborhood in the city. From Hyde Park up to Andersonville and everything in between, I think each has their own individual style. Of course, not every neighborhood has the most mainstream or “style setting” aesthetic but I don’t think that matters. Beauty is in the eye of the beholder.

What do you think sums up Chicago style at the moment? Any specific looks or trends?
To be frank, I think everyone has started to dress like a “hipster”. The indie aesthetic has hit the mainstream and now it’s the thing to do because it’s everywhere. Girls in every subculture are wearing skinny jeans, scarves, and fedoras. Boys in every subculture are wearing Chucks, nerd glasses, and vests.

When taking street style photos, what look inspires you to take a photo of them?
I love interesting details and people. I also veer towards great ensembles. It’s rare that you see someone in a “complete look” but when you do, you know it and it’s a wonderful thing.


What has been a favorite look of yours to photograph so far?
I’m not sure if you mean one person in particular or a specific style. In general, I am not biased. I love taking photos of both men and women in every walk of life as long as they are eye-catching.

How would you describe your own personal style?
My style is pretty eclectic, maybe a little eccentric. I’m not really afraid to wear things that make me stand out like sequins, vintage fur, and bright colors. Though, my daily uniform is generally a basic dress/romper or jeans and a tee paired with a combination of funky accessories. Scarves, necklaces, handbags, big rings, and tons of bracelets. I love it all!

What are your recommendations for some cool Chicago shops?
Some of my favorite shops include:
Eskell: Beautiful vintage-inspired clothing and amazing accessories run by two great gals.
Pivot: Pick up eco-friendly fashion which includes my very own vintage collection, Elegantly Wasted
Hejfina: Out of my price league but super modern and fashion forward clothing.
Penelope’s: Cute and colorful pieces for girls and guys.

Images Sources: The MidWasteland