Outfit Inspiration

What to Wear this Week in Chicago: Athleisure — A Style Your Mom Will Probably Hate

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What to wear this week in chicago

What to wear this week in Chicago

There’s a thin line many walk between individuality and indecorum. The boundaries of both are made matter-of-factly clear by our mothers.

In a time long-long ago, before Uber, people were compelled to take public transportation from here to there. I was one of those people. Growing up in Milwaukee there was no ‘L’, only city busses, the routes and schedules of which were as predictable as a politician’s stance on fundamental issues in an election year. The buses were pitifully unpredictable is what I’m saying. Wishy-washy.

To arrive on time for my summer job shifts at The Gap, I biked it. The entire stretch took 15 minutes down one industrial road. This is back before Patrick Robinson’s Gap. This was still slim jeans, no curvy Gap. Back when Gap had a look and people purposely found ways to incorporate that look into their own personal style. This was Crayola-colored-denim-jacket Gap and I was excited to work there.

My wardrobe consisted of the typical Chanel knock-off aesthetic the brand was going for at the time. Tweed blazers covered in too many of grandma’s broaches, fitted dresses and hot pink denim vests, slim fit pants worn under sweaters large enough to hide a family of cats, and slouchy bleached jeans over crisp oxford button-downs. I took full advantage of my employee discount.

My mom would co-sign these looks with a nod, smile, and the occasional request to borrow something from my closet. I acted like I didn’t care although I was proud she approved.

What to wear this week in Chicago

Eventually, I set my sights on greater employee perks and left my job at The Gap to work as a baggage handler for a national airline — a job that still paid in pennies but included the ‘fly anywhere we fly’ bonus. With this more physically demanding role, my style evolved. I didn’t wear confining blazers anymore. I wore sweatshirts with stretchy skirts, overalls over white tanks, and velour tracksuit — with heels. Admittedly, I looked like a fancy hobo most of the time.

“Why are you wearing pajamas with heels?” Shade is a dish best served cold.

“This is a velour tracksuit, Momma. And it wasn’t cheap.”

“Girl.” Completely baffled, she looked me up and down and just shook her head. My mom has never again asked to borrow anything from my closet.

What to Wear this Week in Chicago

Athleisure isn’t the look of old Chanel. It’s the look of “I have two classes today and then I’m going back to bed” or “I handle bags at the airport for free flight tickets” life. I’m a fan of this look. More importantly, Beyoncé is a fan of this look. Athleisure as a trend is designed to make you look like the gym rat you’ve always wanted to be but without any of the work. Your mom will most likely consider it lazy. A few years from now, you may agree with her.

Since this week in Chicago promises everything from sun to snow, I recommend layering yoga pants with sleeveless coats and sneakers, hoodies with dresses, and track pants with blazers and heels. But don’t listen to me, listen to Beyoncé.

What to wear this week in Chicago

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Kari Herrera is the creator of Chicagoings.com, Chicago’s indie city guide and blog. She often writes about the city’s points-of-interest as experienced by a local. She is a Social Media Marketing Manager and freelance writer. When she’s not working, Kari donates much of her time to the education of French-speaking immigrants in Chicago.

  • Whitney Dosty

    Great read and gooooorgeous pictures! Love the monochrome athleisure style. checkout http://www.onwyattstyle.com to see some of my athleisure styles

    • Oh MY! I LOVE your website and IG feed! You are gorgeous. So much inspiration!!!
      Thanks for reading!

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