Last summer I experienced one of those life-flashing-before-your-eyes moments when you realize you might need to make some serious changes about how you carry yourself. I’m barreling down a street in downtown Chicago – half running because I’m already late for an appointment – and this couple literally stops me dead in my tracks. They seem confused, anxiously scanning their surroundings like downtown Chicago was supposed to spontaneously drop the Bean right there on the sidewalk. “Excuse me, do you know where Millennium Park is?” the woman asks.
I open my mouth to respond, but her husband cuts me off. “No, actually, never mind honey, he’s obviously lost too.” Wait, what? Lost? In Chicago?
I grew up in Chicago. I know where Millennium Park is.
I live like, ten miles from Millennium Park.
I’ve probably walked by Millennium Park like seven hundred times. But there was something about my whole vibe that apparently screamed tourist AF. As in airlines-fly-you-in-from-Denver-this-morning tourist. “What gives it away?” I asked them once we were safely navigating Madison Street without accidentally getting arrested for jaywalking.
He looked down at my outfit and said, “You look like you got dressed for fun in the city.” Ohhhhhhhhhhhhhhhh. Let me tell you about the look I was rocking. White Adidas sneakers (complete with that brand-new-from-the-box shine, which was obviously my downfall), oversized messenger bag bulging with who knows what, and –ugh – this super lightweight jacket with like eight little pockets on it.
Y’all know what I’m talking about, right? Those new-age-y ecofriendly jackets that everybody was wearing in the early aughts? They’re technically jackets, but they might as well have “I’ve never walked a city block in my life” written all over them.
Needless to say, I went through a period of major self-reflection after this interaction. Did I really look like I’d waltzed into Chicago that morning from Des Moines on my vacation from work? Did that really look like my normal outfit?
I felt like Sarah Palin walking into a ballet studio. When I tried to blend in with the city crowd, I actually stuck out like a sore thumb. It was almost comical.
I started scrutinizing dudes that I walked by that looked effortlessly cool and chic. What was their secret? The answer was simple: nothing.
The guys that looked the most comfortable wore literally nothing special. There was my coworker Dave who went to high school in Lincoln Park – every day, he rocks into work in faded jeans that have seen better days, worn-in leather sneakers, and some wrinkled old sweater his grandma probably gave him. He literally throws on clothes and runs out the door and still looks more put together than I do when I spend twenty minutes deciding what to wear.
It’s that effortless-awesome vibe that screams, “I don’t have to try here because I’m already home.” Shoes, man. Shoes are everything. In the city, your shoes are basically your rep.
Bring the wrong shoes and you’re announcing to Chicago that you don’t know the first thing about traversing city sidewalks. Dress shoes and you look like you just stepped off the elevator from a meeting at the Palmer House. Sneakers that look too brand new and you look like you just arrived for your triathlon between brunch and boozy-mimosas lunch.
I actually went through a phase where I would wear running shoes anytime I left my apartment. We are talking Nike CrossTrainers here people. All because some article told me I needed to wear “comfortable walking shoes” in the city.
Might as well wear a sign around my neck that read “Hi, I’m from the burbs and THIS scares me.” Ever since I’ve switched over to stylish-but-worn-in leather sneakers. Or these Chelsea boots I thrifted from Spite Vintage in Wicker Park. The key is wearing shoes that look lived-in, not outfits that scream “PERFECT FOR WALKING AROUND THE CITY!” My girlfriend teases me about having my “city shoes” but whatever.
They’re my Chicago stones if she wants to be cute about it. Same thing happened with my bags. I used to carry around this HUGE black messenger bag with the world nestled comfortably inside.
Laptop? Check. Chargers?
Check. Hanging on my phone charger? Check.
Bottled water? Check. Extra snacks?
Check. Little umbrella? Check.
I looked like I was preparing for downtown Chicago to collapse into the earth’s core any second. People who’ve lived here forever seemed to carry around way less stuff. Because they know where everything is – where to get Starbucks (or better yet, Espresso Shots), where to duck inside when it rains, where to grab whatever supplies they need.
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The city IS your supply chain. These days I throw on my trusty leather portfolio I found at an antique store in Logan Square. Enough room for my laptop, wallet, keys, phone.
Maybe sunglasses if it’s sunny. I don’t feel the need to pack for downtown Chicago like it’s briny Krakens waiting to attack me at every street corner. Clothing itself was another give away.
Until that day, I always wore a giant messenger bag that fit my laptop, charger cords, water bottle, emergency granola bars, mini umbrella – you name it. Not only did my bag look like I was packing for an Antarctic expedition, I WAS packing for an Antarctic expedition. When you live in Chicago, you know how to layer like a professional.
You have favorite wool sweaters that everyone else got rid of because “they weren’t flattering.” You own coats that are weather-appropriate, but don’t have you looking like Bill Murray in a new SNL sketch about Chicago winters. You wear scarves that don’t look like you swiped them from the airport gift shop. As a Chicago transplant, I made the mistake of wearing ALL the colors.
Yellows, blues, whites. Bright colors that seemed to say “LOOK AT ME, I’M IN THE CITY!” But my fellow Chicagoans seemed to stick to more neutral colors. Navy.
Gray. Black. Olive.
Colors that wouldn’t show the grime off the L or look like a crayon box melted all over them. Did you see those photos I was talking about taking earlier? Man, tourists love taking photos in Chicago.
Problem is, they’re doing it like they’re taking evidence photos for the police department. I can’t tell you how many dudes I see walking backwards down Michigan Avenue staring intently at their phone screen like they’re about to discover the next water cool. You can’t TAKE pictures in Chicago.
You appreciate your surroundings and notice the beauty WITHOUT having to whip your phone out and catch it for prosperity. Unless we’re talking about rain jackets. In Chicago, weather-appropriate clothing is ESSENTIAL.
Unless you want to freeze your ass off or melt like Beyonce in Dragon Ball Z, pack those Timbs and wear a jacket. And when I say wear a jacket, I don’t mean these crazy-colored Gore-Tex adventure coats that scream TOURIST PRESENTS. Weather coats here tend to be flat-black and function over fashion.
Take it from my neighbor Matt who grew up right outside of the city. “You don’t see grown ass men walking around here with shiny new rain jackets,” he said. “Looks like you’re not used to this sort of thing.” Good point. I actually bought one of those bulky parkas last winter because I was prepared to freeze my ass off. Never again.
Honestly, the biggest adjustment I had to make was walking speed. Every city has it’s own pace. Chicago certainly is no exception.
Amble too slowly and with a confused expression? Tourist. Speed walk like you just might miss your destination?
New in town. The dudes that looked most like they belonged moved with a certain swagger – like they knew where they were going, but didn’t have to rush to get there. I think it took me almost a full year in Chicago to truly master that walk.
Friends of mine say they got where they are by dressing like they weren’t trying to dress for Chicago at all. There’s no such thing as “city clothes.” Dress like you don’t know anything weird is going to happen. Dress like you don’t need “weather appropriate attire.” That’s what the girls at work told me when I asked them about their uniform.
It’s genius when you think about it. Because who cares if your outfit is trendy in Chicago? You just want to dress like you LIVE in Chicago.
Don’t get me wrong, there’s absolutely nothing wrong with looking like a tourist when you’re a tourist. Some of my favorite trips have involved feeling horribly out of place in new cities and countries where I didn’t know the rules.
Chicagoans aren’t off limits!
But there is something incredibly satisfying about looking like you belong in Chicago when you’ve been there your whole life. Or at least looking like you know where the fuck you’re going. I asked a bunch of my Chicago-residing pals what it was that made them look so dang stylish all the time.
And what they all said boiled down to one common theme: act like you’re not ACTING. “You just want to look like you randomly ran into that cute barista at Starbucks, not like you’re checking ‘Go Cubbies’ off your tourist bucket list.” -Jake D., beloved actor/dog owner extraordinaire. Sound familiar? The more I tried to look like a “true Chicagoan,” the more un-Chicagoan I actually looked.
It’s like that saying about don’t think about elephants. Right around the time I stopped worrying about looking like I belonged, I finally did. Trust me, it feels great.
Plus I look awesome throwing down Sunday drinks with my friends at Boom Boom Room and knowing exactly where to find the hidden entrance. Because that’s what REAL Chicagoans do.
