You always look so dapper! What’s your secret?
No secrets here! I wear clothes that tell a story about me on that certain day. I find style to be a powerful tool of perception—and I use clothing to create a reaction in others. I like to play with that perception, depending on the day.
What story are you telling?
I know that when I go to a city fashion event, I want to represent a more dressed-up Ryan. That event isn’t about me—it’s about the talent in the industry, so I went with a more classic palette—rather than showing off all my tattoos and such, which causes a certain level of attention. I played with my favorite colors and always love to break the “rules” of fashion though there aren’t any real rules anymore—so wearing a bit of brown with black adds a good contrast to the outfit and a pop of blue adds some freshness.
What kind of reaction do you usually like to create?
It depends on the day, the environment and the audience. I use my tattoos like accessories and can show more of them to get a more shocking reaction from people. For example: if there is a fancy event at a boutique, I may simply wear a black t-shirt and let my tats do the talking. Wearing an outfit that doesn’t fit the spirit of the event can be fun, because all eyes are suddenly on you, even though all you are wearing is a tee. It can be used the other way, as well—like wearing a bowtie or a cummerbund to an event that is more casual. Suddenly, you’re the best-dressed person in the room—and that’s never a bad thing.
Where do you shop for clothes here in Chicago? Any local designers you recommend?
Locally, I love Notre shop in Andersonville for interesting and exclusive menswear finds. I’m a big fan of BOGA for good fit and casual business gear. For those big boss days, Oliver & Rowan Bespoke makes the finest suits in Chicago, if you ask me—and Glass House Shirtmakers fills in the blanks with beautiful shirts and men’s accessories, mindfully made. And, I guess I do have a secret: Forever 21 men’s. The clothes fit my frame (same with Zara—another favorite of mine) and they’re great for mixing high and low styles on an entrepreneur’s budget!
What products do you use to style your impeccable pompadour?
I rarely cheat on Pete, my barber at Belmont Barbershop. He calls me “Hollywood” and literally cuts my hair in fifteen minutes. The best fade in the city! I have three products, depending on the weather: for a softer look, I use American Crew pomade; for a more matted look, I use Imperial; for windy/rainy days, I sport Suavecito Original Hold. I’d be lying if I told you I didn’t use hairspray. I got my first bottle in years and I’m addicted to the extra volume, dammit!
Where do you go for style inspiration?
I’m inspired by my friends, first and foremost. There are really influential pockets of underground style that start to inspire looks that spread and evolve into trends. I keep an eye there, so I know what’s going on, but my own style isn’t particularly fashion-forward. I appreciate a very clean palette (gray, navy blue, black and white are my go-to colors), and I like a classic look (bowtie, suit, black denim and a good shoe) when I dress up. For more casual days (which happen much more often now as an agency owner!), I like a good t-shirt, denim, Chuck Taylors (which I’ll wear with anything), and a flat brim hat. A cardigan is also an easy go-to piece of mine. Furthermore, Tom Ford is one of my style idols—and Alexander McQueen. What a beautiful mind he had; such powerful talent. I keep an eye on the streets and like so many others, I’m constantly inspired by my social media family and the things that float across my newsfeed.
Where do you like to people watch here in the city?
My favorite neighborhood is the one I live in, Uptown. So many things are changing every day here. It’s exciting to be part of it and to watch it come alive in ways it never has. My favorite time is around 7am. I grab a coffee from Heritage Outpost and sit out front, checking email and watching the world head to work. Tied for my favorite ‘hood is Pilsen. I lived there for a couple years a while back and the energy of that neighborhood is awesome. So many artists and so much art/inspiration to discover as you walk from block to block.
In a few words, what’s your style philosophy? How about your life philosophy?
For style, one I always say is something like, “If you dress like the CEO, people will think you are.” As mentioned above, I love the power of style and perception—the art of dressing to create a story of who you are in someone else’s mind. Dress for who you want to be today, or for who you want to be tomorrow. For life: I’m finally, at age thirty-three, discovering a relationship with myself that has quickly become the most guarded relationship in my life. I’m learning that the more I love myself, the more confident I become in my choices. My happiness is number one, and I guard that happiness with ferocity. For the record, me and myself are very happy with each other these days—and there’s nothing better than knowing I’m finally looking out for Ryan. ‘Cause I think he’s pretty cool.
—Interview and photograph by Isa Giallorenzo