The Story Behind the Chicago Handshake (and How Transit Tees Made It Iconic)

The Chicago Handshake, a bold, gritty combo of an Old Style Tallboy and a shot of Jeppson’s Malört, was born in the dive bars of Ukrainian Village. Designed to leave an impression (for better or worse), this unpretentious pairing became a badge of honor for locals and quickly spread from city taverns to daaa burbs.

One night at the dearly departed Flat Iron bar in Wicker Park, a designer from Transit Tees was struck with inspiration. Noticing the regal shields on both drink brands, they merged the iconic imagery into a fresh design—a tribute to a drink that could only be Chicago. What came next helped cement the Chicago Handshake’s place in pop culture.

That inspiration became The Chicago Handshake Drinking Card Game, Transit Tees’ first-ever drinking game. It quickly became a fan favorite, introducing the brand to a new audience. You can shop all of Transit Tees’ Chicago games here, or in-person at their Wicker Park and Andersonville shops.

The success of the game caught the attention of Old Style’s brand manager, sparking a powerful local partnership. The first collaboration? Reviving the Chicago Handshake Challenge, a citywide bar crawl celebrating the now-iconic combo.

To mark the occasion, Transit Tees launched an entire Chicago Handshake Collection featuring apparel, accessories, barware, and home décor, all designed with tavern-inspired charm.

Building on that buzz, Transit Tees dove into Old Style’s visual archive to create fresh designs that pay homage to decades of branding. The results? A nostalgic line influenced by stained glass signs, vintage mascots, retro video games, and even graveyards.

And of course, no nod to Old Style would be complete without the Old Style Tavern Sign Light Box, a replica of the beloved sign that’s acted as a beacon to thirsty Chicagoans for generations. Transit Tees’ own Kyle John Hollings helped bring it to life as both a LED Lightbox and a Tin Tacker.

Want to see more? Follow Transit Tees on TikTok, Instagram, Facebook, YouTube, and Pinterest for behind-the-scenes peeks, design drops, and true Chicago storytelling—straight from the source.