Travel Style: Fall Fashion From The Windy City

By Sola Onitiri

Photographed by Sola Onitiri

Photographed by Sola Onitiri

City of Philadelphia, if you’re listening, close your ears because I’m about to say something that I never thought I’d say. Chicago feels like home. Between the rich neighborhoods, the incredible restaurants and the awe-inspiring skyline that sits on the lake, I understand sticking with this city even in the blustering winter.

Now that we’re finally creeping towards fall, I’ve also noticed that the style on the streets is blossoming. As a recent Chicago convert, I thought I’d reach out to a Chicago style expert, Lauren of @thefashiondailies about what fashion lovers should expect of Chi-Town during the fall. We chatted about her personal style, why fall is so amazing in the windy city and her ideal fall day. Check out her answers as well as our photo shoot in Pilsen below.

Photo by Sola Onitiri

Photo by Sola Onitiri

Describe your style. How did you cultivate it and has it changed as a result of living in Chicago? 

 Oof! Questions like this are always so hard to answer. I feel like 90% of my life is just me playing dress up. So many of my outfits are inspired by tv characters or characters from movies I’ve seen. Is that weird?

One specific thing I do notice about my style is the mindset MORE is MORE. I love mixing patterns with patterns and bright colors with other bright colors. If I can make people think “huh, why have I never though to wear those things together” then I’m doing it right! 

I’ve always been a huge discount shopper so discovering my knack for vintage shopping in Chicago has really molded my style into what it is today. A lot of what I wear is one-of-a-kind so there’s a feeling of wearing something no one else can that makes you feel like an OG badass.

 How would you describe Chicago's style as a city? 

Chicago is a super trendy city! I think it’s funny how each area of the city kind of has it’s own aesthetic. If you’re wandering around Gold Coast you’ll see a lot of designer bags, straight-off-the-runway pieces, things like that. In Wicker Park they’ve got the whole Dr. Martens with ripped jeans and a band tee. River North for the most part (my hood) is a lot of Tory Burch and pointed ballerina flats. Everywhere has it’s own spice! 

The great thing about Chicago is that you don’t have to identify with one specific style or look. I’ll tailor my outfits based on where I’ll be going out. If I’m going to a concert in Logan Square I’m going to pick a vintage snakeskin handbag over the Chanel boy bag. Brunch in West Loop is a completely different outfit than Cocktails in Pilsen. It’s fun to get that flexibility to re-invent yourself everyday.

Chicago Street Style

“The great thing about Chicago is that you don’t have to identify with one specific style or look.”

 Does your style change in the fall? If so, how?

I definitely incorporate different materials into my wardrobe for each season. For fall and winter I’m all about velvet, faux fur and layering. I feel like a jacket or coat is the perfect accessory to pull a look together. You can elevate a simple t-shirt and jeans combo with a pair of printed ankle boots and a neon orange coat. Throw on a cool hat & edgy sunglasses and you’ve taken your look from 0 to 10.

What's the best thing about Chicago in the fall?

Hot coffee!! I mean, this isn’t specific to Chicago by any means, but for me, this is what makes fall. I’m a coldbrew kinda gal- I’ll drink iced coffee year round but it truly feels like fall once you have that hot cup of coffee in your hand and you’re walking around the city. I grew up in the Midwest, so I’m used to experiencing all four seasons. That’s not so much the case here- we go from 80 degrees and sunny to straight up winter. It’s kind of magical when that change happens because it’s normally overnight and it’s like you wake up and you’re in a different city. The air smells different, the trees have changed, it’s just the best!

Travel Street Style - Chicago


Describe the ideal fall day. Where are you going and what are you wearing?

The ideal fall day for me is pretty simple! I like to start my days with some sort of productive activity. It generally isn’t a workout, but it can be something like running to the grocery store, walking to get a coffee or juice or just going for a leisurely walk. I love watching football and just the socialness of having games on constantly, so I love to pick a sports bar and head there with my friends. Depending on who we’re cheering on, there’s likely a bar for that team! I feel like my fall go-to outfit is going to be vintage Levi’s, a cropped sweatshirt or sweater with cool Nike kicks. Cozy, versatile and again, easy to edge up with a moto jacket and a pink beret.

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