We spotted this sneakerhead in Chicago’s eclectic Wicker Park neighborhood. He agreed to chat with us about the trendy chukka boots on his feet, his time hiking in Air Jordans, and the craziest thing he’s done for a pair of kicks.
Name: Chris M.
Current city: Chicago, IL
What do you do?
I’m a writer for a hip-hop and fashion magazine.
Are you one of those guys that hates shopping?
No, I definitely enjoy it. I’m an impulse shoe buyer—it’s almost like a problem. If I see a pair of shoes I like on a website or a blog, I go hard to get them. I also joke about how shoes “speak” to me—I’ve stopped in my tracks and gone into a store to buy a pair that’s caught my attention more times than I can count.
Couldn’t agree more. What’s the craziest thing you’ve done for a pair of shoes?
I used to collect sneakers from 2004 to 2008 and I would literally camp out for a day or two, sometimes more, just to snag a pair.
What are 3 pairs you absolutely cannot live without?
How do you change up your style between a date night vs. a night out with the guys?
Well, I’d dress smarter and less athletic on a date. I’d wear something that works with a cuffed pant—maybe a pair of wingtips. Although I should probably add that I don’t like refined, hard-bottomed shoes, so when I say a pair of wingtips, I mean a more rugged pair with some cool detailing or a chunkier sole. When I’m hanging with the guys, I’m thinking about comfort, so probably my Air Jordan 1s or a pair of Nike sneakers.
Tell us about that one pair of shoes you own that has stuck with you through the years?
It’s an interesting story actually. I was looking through some old class photos the other day and I found a picture of me in the 2nd grade wearing a pair of classic Timberland boots. I don’t own that particular pair anymore, but I do have the same shoe in my size that I wear all the time. It’s pretty cool how they’re such classics; they really have that style on lock.
Tell us about a memorable moment you’ve had in your favorite pair of shoes?
I recently took a trip to Ecuador and hiked the Inca trail… in my Air Jordans. They went from being red and white to red and brown. I still haven’t washed them because every time I look at them, I’m reminded of my time there.
What made you pick a pair of Jordans to go hiking?
I thought it was going to be a casual walking tour, but it turned out to be a 2-mile, 14,000-ft. hike. There was this dude decked out in Patagonia gear who slipped in a puddle, and there I was dominating in my Jordans.
What do you like doing in your free time?
I’m a writer by profession, but I love it so much, it’s also what I enjoy doing when I have some time off. Whether it’s little thoughts that strike me on my commute, poems, or a rap—I’m always putting pen to paper. I also like to draw and play basketball when the weather permits.
What’s one tip you’d give guys going into spring?
Lose the socks; don’t be scared to show some ankle.
Love Chris’ look? Try these on for size:
Clarks Bushacre Chukka Boot $79.95 (Compare at $100!)
Original Penguin Merle Chukka Boot $109.95 (Compare at $165!)