The Bears Jeffery Simmons Welcome To Chicago Monster of the Midway Shirt is for Bears fans who felt the jolt on October 29, 2026, when Chicago traded for the All-Pro defensive tackle from the Tennessee Titans. Wear it to Soldier Field, a prime-time watch party or the tailgate lot while Simmons settles into navy and orange and the Bears chase their first Super Bowl title since 1985.
Bears Jeffery Simmons Welcome To Chicago Monster of the Midway Shirt – The Midway Got Meaner
The Jeffery Simmons Welcome To Chicago Monster of the Midway 2026 Shirt uses a loud, retro, bootleg-style graphic, the kind of collage design that recalls 90s rap tees and vintage sports posters. It’s set on a black shirt so the white, orange and navy pop.
At the top, “WELCOME TO CHICAGO” arches across the chest in tall, condensed white block letters with a bright orange outline. The banner shape works like a stadium marquee, announcing the arrival before you even reach the player. Behind it sits an orange line drawing of the Chicago skyline, with the city’s signature tower silhouette rising in the background, which grounds the design in the city.
Flames climb up behind the skyline and frame the center of the graphic. Two portraits of Simmons in Bears navy and orange anchor the design. On the left, he’s helmeted and mid-roar. On the right, he’s bare-headed and screaming, with arms flexed in a celebration pose. Together they show two sides of the same player: the one opponents see across the line and the one teammates see after a sack.
Below the artwork, “JEFFERY SIMMONS” runs in heavy, slanted white lettering with an orange outline, sitting on an orange bar that gives the name weight and a sense of motion. “MONSTER OF THE MIDWAY” closes the design in clean, spaced capital letters, a quieter tagline under all that energy.

Overall it reads as intense, celebratory and unapologetically Chicago. It fits game days and bar watch parties, and works just as well as a casual statement tee any day of the week.
Product Details
- Style: Unisex crew neck short-sleeve T-shirt
- Design: “Welcome To Chicago” arched header, Chicago skyline outline, flame graphics, dual Jeffery Simmons player art, “Jeffery Simmons” nameplate and “Monster of the Midway” tagline
- Fit: Classic unisex fit
- Origin: Proudly Made in the United States
- Care Instructions: Machine wash cold inside out with like colors. Tumble dry low or hang dry. Do not iron directly on the print. Do not bleach.








produit de qualité
The Jersey is great
Wow, all three! Website was standard e-commerce, customer service promptly responded to my questions twice — though a bit indirectly, delivery tracking was a bit of a black box but once item cleared New Jersey customs I knew it was on its way.