So when I headed west to Wicker Park last weekend, I expected to only see skinny jeaned, flannelled hipsters roaming the streets with their oversized headphones and angsty expressions. And although I did see the skinny jeans and they were disturbing, I also saw the flannel and kind of fell in love with it.
That is Wicker Park to me, true to its hipster stereotype but still strangely lovable. Loosely defined by the Chicago river and Western Ave to the East and West and Bloogingdale and Division to the North and South, the heart of Wicker Park is really Milwaukee. That is were you will find all the thrift stores a hipster could ever want plus Reckless Records, one of those record stores you can wander through for hours without anyone asking you if you need help because they know you are not shopping you are experiencing.

There is also the smattering of bars on Milwaukee and down to Damen. I had the privilege of briefly experiencing Rainbow Bar on Damen before the crush of tipsy trendies pushed me to a quieter bar down the street called Easy Bar. From the Rainbow Bar complete with creepy baby doll image on the wall and sizing up glances at the front door to Easy Bar, the quieter gap/j crew crowded bar down the street, Wicker Park lives for the hipsters but indulges the rest of us as well.
Like a lot of neighborhoods in Chicago, Wicker Park has evolved to become the hip community it is today. It has seen brewery owner’s mansions in the late 1800’s, an influx of Puerto Rican immigrants in the 50’s, followed by a round of gentrification and then invasion of artists in the 90’s. And like most Chicago hoods, Wicker Park is welcoming even to those less trendy.
The key lesson of Wicker Park is timeless: don’t knock flannel until you try it.
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