Trip Report: Chicago, IL

No, I didn’t backpack through Hyde Park or bushwhack Lollapalooza. The following is an unconventional trip report by Bivouac standards:

On Friday May 29, 2015, I boarded a 6am Amtrak to Chicago Union Station to visit friends at Northwestern University in Evanston, a suburb of the Windy City. They all had class until 7pm, and my only choices for trains were 6:40am (arriving 11am) or a 7pm (arriving 11pm). Essentially, I’d have 6 hours to kill in the greater downtown Chicago area before I met my friends. Train Wi-Fi in hand, I loaded up the /r/malefashionadvice Chicago Shopping Guide and chose a few interesting shops in the Loop and Gold Coast areas. I wanted to see the best Chicago had to offer.

I hit the ground running at noon on a beautiful summer day – 65 degrees, partly cloudy, slight breeze, and bright sunshine. A real Chamber of Commerce day. With all the walking I was going to do, I wanted comfortable, good-looking clothes that would also keep me cool. For a day in the city, I wore a white Lacoste crew neck pima cotton tee, Original Penguin navy chino shorts, and Sperry 2-Eye Authentic Original boat shoes in Sahara leather – laid back, but well-fitting casual style in a strong color palette.

From Union Station, I walked to Chicago’s premiere shopping destination: Oak Street, a relatively-quiet street in the shadow of the “Magnificent Mile” along Michigan Avenue.

Compared to the Mag Mile, Oak Street is contained, sparsely populated, and well, pleasant. Traffic hums by and manicured trees line the roadway. Every few feet, a single marble sidewalk paver announces a building’s tenant and the picture snaps together. Oak Street is home to the Chicago flagships of Hermes, Bottega Veneta, Moncler, and more. Internationally famous designers lay their Midwest roots on Oak Street, and dozens of independent boutiques stock rarities from the rest without their own store fronts.

The “flag wall” at Independence, Chicago.

The first stop on my Oak Street pilgrimage was Independence, a menswear and Americana boutique on the second floor of an otherwise inconspicuous brick duplex. Walking inside is like swinging open the oak doors to Teddy Roosevelt’s hunting cabin: sun-bleached American flags, handmade leather boots, and raw denim from the world’s most coveted brands line the walls and shelves.

Stainless steel camp mugs, horsehair brushes, and handstitched loafers on the same shelf. This is my kind of store.

Jeans from Levi’s Vintage Clothing share rack space with Norse Projects sweatshirts and Kapital flannels. As a poor college student, I could only ogle and talk shop with the extremely knowledgeable and helpful staff – to try anything on would’ve been an affront to the pieces they carry. I talked denim, boots, and music for close to an hour with Iicky, a local denim artist (seriously, check out his stuff – it’s incredible) who has the privilege of working there. If you go to Chicago, go to Independence.

I was wowed. What else could Oak Street provide? Referring back to my reddit guide, I next stopped inside Moncler. Moncler is luxury goods shaped by outdoor technology. Goose down, breathable technical fabrics, and functional details are common features of staple citywear pieces. Unfortunately, I wasn’t allowed to take pictures of the inside – but believe me when I say that the store was gorgeous.

I had walked the length of Oak Street and with an eye on my watch, decided to head back towards a Purple Line stop to eventually get the L north to Evanston. However, a gold-leafed monolith stood between and catching that train: the Ralph Lauren Chicago store. I was drawn in by the conservative exterior, ornamented only with an etched “Ralph Lauren” in gold above an awning to the street. Interested, I pushed a massive open door into a world removed from the sirens and noise of Chicago, 2015.

This is understated for Michigan Ave.

I have to hand it to Ralph Lauren: for the brand that invented America’s preppy fantasy, they’ve certainly practiced and nailed presentation. Hardwood paneling, fresh flowers, and decadent polished marble all sit perfectly lit under antique brass fixtures. A grand staircase lined with portraits of important looking people and their groomed children separates the main floor from “sportswear and suiting”. Imagine Downton Abbey meets the Hamptons circa 1930. It is an aristocratic mansion designed and manufactured to sell clothes. And it is beautiful.

I’m convinced that every portrait’s subject was either really important or could just look the part. And isn’t that half the battle?

I walked around in awe, took tons of photos without interruption (@Moncler), and tried on a sweater that cost more than two month’s rent. Even as I left empty-handed, there was this funny feeling that I should have spent money there just to fit the ambiance they had so expertly created. The landed gentry portraits along the staircase would have wanted it, but on a full time student budget, all I could take home was a business card. Moral of the story: stay in school, kids. Then you can enjoy the finer things in life AND keeps the light on.

Pictured: the finer things.

It was now 5:30pm, and I had to make my way to the Lake/State Purple Line to ensure that I could meet my friends for timely dinner an hour’s train ride away. That gave me just enough time to get a pour-over at Chicago staple Intelligentsia Coffee – a delicious afternoon pick me up after a whole day on my feet.

I had a single of the daily special, a single origin Costa Rican coffee with notes of fruit and caramel. For those of you in Ann Arbor, our friends at Comet Coffee (also in Nickel’s Arcade) serve Intelligentsia beans with the same pour-over methods as you’d find at the company stores. The coffee is just as incredible, I swear.

If you’re in Chicago, check out Independence, Moncler, and Ralph Lauren and be sure to try Intelligentsia Coffee! I highly recommend each.

~Alex R. -Men’s Fashion

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Planning a trip? Want to get more insider tips and travel recommendations from Bivouac’s expert staff? Read about our adventures to Canyonlands National Park (UT), Pictured Rocks National Lakeshore (MI), and Mt. Adams (WA), or click here to go back to the Bivouac Blog!