Chicago Motorcycle T-Shirts & Apparel

Stand at Adams Street and Michigan Avenue and look south. That green 'Begin Historic Route 66' sign above the intersection is the start of 2,448 miles - the most ridden road in America begins right here, under the shadow of the L tracks. Chicago riders know what that corner means: every westbound run, every cross-country story, every solo ride to Santa Monica traces back to this block. The design is built around the city that sends those riders out. Original Chicago biker shirts, printed on heavyweight ring-spun cotton, shipped to riders in over 70 countries.

Four Stars, the L, and the Mother Road

Ride the Loop at night and the L tracks throw a grid of steel shadows across the street under your wheels. That iron lattice is the backbone of this design, and we hung the city's four red stars over it - drawn raw, no civic border, the way riders here wear the mark on helmets and tank bags. Below the stars sits the Route 66 start sign at Adams and Michigan, the corner every westbound run out of this city traces back to. The banner reads 'Mother Road starts here.' Four stars, one lattice, one road pointing south to Santa Monica - that is the whole story a Chicago rider carries on their back.

Materials & Who It's For

This one is for the Chicago local who rides the lakefront and already has the flag on their tank bag, and for the out-of-towner who flew in to start a Route 66 run and wants something to mark the beginning. It also lands as a bucket-list gift for the rider planning to do the full 2,448-mile haul from here to Santa Monica - something to wear at the start. Tees are heavyweight 5.3oz ring-spun cotton, side-seamed and pre-shrunk. Hoodies are 8.0oz cotton-poly fleece with double-needle stitching at the stress points. Caps use raised embroidery on a structured six-panel. Every piece is checked by hand before it ships and tracked to your door in over 70 countries.