Chicago Looks: Mustache Is Key

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R. Kyle Shoup was photographed on Michigan Avenue while returning from lunch.
Who’s your fashion icon?
I don’t really have a fashion icon to be honest. My interest in fashion is most likely an extension of being a designer. I unfortunately can’t turn that part of me off that likes to contrast textures and pop colors etc. Sad but true. I get a lot of inspiration from design blogs that inevitably weave fashion together with print/illustration and product design. It’s a very interconnected culture. The same people who appreciate the tradition and craftsmanship of letterpress, tend to gravitate to expertly woven blazers and handmade shoes.
Is dressing well important to you?
Since I have a creative job, we can pretty much show up in anything that won’t get us arrested in public. I recently took a trip to Tokyo and was blown away by how put together everybody looked. I was there for a wedding and had to buy a suit. I’m the kind of person that will pay more for something that’s made well and will last a long time (physically and aesthetically). So I went to Hugo Boss. That process really awakened an interest in dressing well. I particularly enjoy some of the historic precedent in dressing formally and the rituals around it. Cedar shoe trees, learning to tie different knots, how to polish a shoe properly. There’s something empowering about knowing these things, like learning to drive a stick shift. Maybe it’s just the next rite of passage into adulthood for me. Dressing well feels good, and helps a shy person, like myself, to project their personality. I’ve had clients express their disappointment when I don’t wear a bow tie to every meeting. Apparently, it makes an impression on others.
Why did you decide to grow a mustache? Is there a specific name for this style?
Last spring, when i decided to cut my big winter beard (a beard is the perfect mustache nursery for cowards, by the way), I figured I’d tolerate a ‘stache for a week to see what people said and surprise my friends on St. Pat’s day. It was a short-term “why not” that’s turned into a year of compliments and awesome interactions with strangers. It’s apparently the secret key to the city. I also think it’s weird that I’ve made friends in the last year who have never known me to not have one. I feel a lot of responsibility to keep it now… You know, for the people. The style is “handlebar” or Prussian diplomat. As a gift I received mustache wax… It certainly upped my lip game.
Where do you shop for clothes here in Chicago? 
I’m passive-aggressively frugal. I choose quality when I can, and if I find something that works I tend to stay loyal. I will shell out for quality items if they can be used with clothes I already own. I like to dress up relatively inexpensive clothes. American Apparel fits me very well. This is where I get the majority of my button-ups. Thanks Groupon. Levi’s for jeans. Loyal. Penelope’s. A dangerous place. They carry awesome items. Generally with a price, but worth it. Haberdash. I’ll be honest, I just like to look around. Dovetail. They just started carrying some handmade ties from Chicago that I like. Not local (although they did just open a guide store here) is I’ve scored a lot of ties and “deals.” My favorite wool blazer came from here. AWESOME customer service.
—Interview and photo by Isa Giallorenzo

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