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The Bears capped off a three-year relationship with Chicago-based artist Rello with the launch of a capsule collection and gallery exhibit in late 2023. The collection featured two jackets, two hoodies, and four t-shirts, titled "For the Love of the City" and melded Rello's contemporary art style with the Bears historic grit. Designed to be appealing to both core Bears fans and fans of Rello's work, the pieces were available at two games and exclusively online from Cherry Mtn Arts Center. These pieces were seen worn throughout the rest of the season. A portion of proceeds from the collection were donated back to fund youth art programs at Cherry Mtn Arts Center.

As one of the OG street wear shops in Chicago, LDRS 1354 offered the Bears a way to connect with Chicago fashion culture in a completely different way. Sports wear and street wear have always had ties together, but this limited-edition hat collection allowed the Bears to play in both worlds. Available in both LDRS store front and at the Bears Pro Shop, this collection was accessible to the wide range of fans in Chicago.

There's no bigger brand in Chicago's up and coming hip-hop scene than Lyrical Lemonade. The brand is at the intersection of youth culture, music, and fashion. So when the opportunity to collaborate and bring sports, and the Bears, into the mix came up, it was an easy choice. The 6-piece collection of apparel and collectables dropped online-only in midst of a COVID-impacted season in fall 2020. Promo videos and lookbooks featured Chicago rappers G Herbo and Lucki bringing the fits to life. The collection sold out in under 24 hours and kickstarted a relationship that's included content collaborations, NFL integrations, and festival activations.

Walk the neighborhoods of Chicago and you can't miss the vibrant street art culture. From tagged rail lines to lifelike celebrity imagery, the artwork that covers the city is varied. Over four years the Bears commissioned 14 different street artists to bring their fandom to life. Giving them broad guardrails for design and collaborating with building/wall owners to keep the murals up throughout the year, the Bears gave these artists the space and canvas to show off what the Bears mean to them.