Featured Project: Chicago Humor

Brand Positioning
Messaging Strategy
Content Strategy
E-commerce Design
Front & Back End Development

There's something so genuine about Midwestern humor. The way it strikes that delicate balance between self-deprecation, honesty, and congeniality makes it accessible to everyone, no matter where they're from. 

That humor is in our DNA as Chicagoans, which explains how an idea for a funny t-shirt at an office pizza party grew into the beautiful side business that is Chicago Humor

Taking the (Polar Bear) Plunge

When we decided to go all in on creating a t-shirt company, we took on a big challenge. To do Chicago Humor right, we knew we'd need to produce an entire identity system, a content strategy, an e-commerce platform, a guiding aesthetic, a thoughtful customer experience, and a marketing strategy. Fitting it all in alongside our client obligations would be no small feat—but it would be a fun one. 

Finding the Punchline

To kick things off, we dove into our work like it was a deep dish pizza from Pequod's, brainstorming t-shirt ideas and brand messaging together. From politics to the weather, Chicago has no shortage of fodder. Once we nailed the tone—that of a hardened Chicagoan telling it like it is—we made sure that brand of humor permeated everything from website calls to action to marketing materials to photography.

Bold Like Daley, Humble Like Pre-2016 Cubs Fans

With our humor compass set, we moved on to create a lively, flexible design system that would convey those one-liners perfectly—and that would feel coherent even with multiple designers bringing individual styles and aesthetics to the work. Bold, in-your-face fonts elevate the irreverent catchphrases, and an ever-present smiley face logo balances lightheartedness with a dash of dark humor: critical to achieving that Chicago-style humor. That balance mirrors the messaging, which skews honest and just a bit confrontational. The shirts—and the website—have all the trappings of being created by a jaded Midwesterner with a heart of gold. You know, like us. 

Keep It Simple, We Still Have Day Jobs

The Chicago Humor site runs on Shopify. It's the industry standard for a lean, easy-to-manage platform, and it perfectly suited our needs. We designed and built a custom template for control over both the user experience and the look and feel of the site. Shopify's structure makes for easy browsing on the consumer side and easy content maintenance on ours, and we're excited about its site behavior-based email marketing features. We're able to message our shirt shoppers when they abandon a cart, don't use a promo code, or place their first order. 

Always Test Those Assumptions

We're pretty sure we've tapped into three things Chicagoans are passionate about: Chicago summer, area codes, and putting the Chicago flag on anything and everything. But validating our theories is the ODC way, so we've created an initial run of unisex shirts and tanks to test the waters. And, like the polite, generous Midwesterners we are, we developed humorous thank-you notes and stickers to accompany each order. 

A Brand Bill Murray Would Invest In

What did we turn out? An irreverent, honest online retail brand that Bill Murray would (should) invest in. The shirts take aim at Chicago’s idiosyncrasies while celebrating the best city in the Midwest. Bold, colorful type and catchy illustrations on unisex tees mean we've created something for everyone, from downtown to the ’burbs.

What’s Next? 

This is where you go to www.chicagohumor.com and buy a t-shirt. Thanks for supporting us.  

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One Design Company is a research-driven design and development studio. For over a decade, we’ve explored the intersection of experience and technology—where powerful brands come to life. Want to learn more? Let’s chat.

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