What do you wear to Chicago Festivals?

What do you wear to Chicago Festivals?

Summertime is that time where we can finally where skirts and dresses and open-toed shoes. We don’t have to carry coats (just umbrellas) and you can actually be outside and show your whole outfit instead of covering it up buried in a coat, gloves, scarves, boots, leg warmers…..

I’ve been spending summer wearing black – but there’s nothing like the colors and the patterns and the style of Chicago summers.

So, in honor of this coveted time in the city, I’ve worked with Emily Bricked Edelson, Co-Founder and Illustrator of Chic Sketch, a fashion forward mobile app that sketches photos into Instagrammable fashion illustrations by real fashion illustrators in a matter of minutes.

She’s helped me see the beauty of summertime style from ruffles to vests to white dresses.

Edlemson shared some of her favorite trends and prepared special sketches exclusively to showcase Chicago festival season style.

“I always look at other it-girls when I’m in need of style inspiration like Olivia Palermo, Alexa Chung, or Kendall Jenner. My style is feminine with edgy touches. I’ll pair a cute dress with a leather jacket, or jeans with stiletto,” said  Edelson, “My personal style is all about taking trends, and adding a New York touch to it.”

Summer Rooftops in Chicago:

In the midwest, the one thing you will notice from Memorial day to Labor day is that Chicagoans embrace white – white pants, white dresses, white shirts.

White is summer’s must-have color. It’s perfect for a day at the beach, rooftop parties and work events.

Emily Bricked Edelson took this trend and sketched some of her favorite looks!



Chic Summer Patterns:

But a color is not the only thing that marks summer style. It’s also patterns. And one of Summer Sixteens summer fashion is the the scallop trend as part of a feminine detail on a leather jacket, and a fun twist to a pencil skirt.


Chicago Festival Fashion:

But in Chicago, while we dress up for work and rooftops, the real fashion staples are in what to wear at Chicago festivals. So, I asked Emily Edelson to sketch some of her favorite outfits and trends to wear to Chicago festivals. Below are some of my favorites, but be sure to subscribe to the Windy City Cosmo newsletter to see more chic sketches from the chic Illustrator herself.

dress 1

dress 2

Edelson is known in the fashion world and her sketches have even been displayed in the coveted 38th and 5th Avenue in New York City. Her co-founder comes from Appetizer Mobile, which has designed and developed over 150 apps for world class brands such as, Lady Gaga, Kim Kardashian, NBA Properties, Epic Records, ZocDoc, Montessorium, Universal Music Group and Interscope Records. 

After a year of launching their start-up, Chic Sketch has been used at fashion and beauty events by global brands like Sephora and for the everyday girl via a simple app download.






Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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