As Pittsburgh and surrounding townships started taking shape, an enterprising farmer named Thomas Aiken dreamed of a thoughtfully organized neighborhood plan where his farm stood. Convincing the Pennsylvania Railroad to create a dedicated station made the dream a reality (with some advocation from Andrew Carnegie). Shadyside Station was added to the Pennsylvania line and the tuscan red train cars started making dedicated stops in 1860. That same tuscan red is featured as the color of the shirt.

That same year, the Shadyside Presbyterian Church got its start and quickly became the heart of the neighborhood. The current church was built in 1890, serving as the third building to house the congregation. The current church serves as as the featured graphic of the shirt.

Lastly, the oaky bark color of the graphic is a quiet reference to the most likely origin of the neighborhood name. Many credit Caroline Aiken for inadvertently naming Shadyside, but we can infer that the abundance of oak trees in the area had a greater influence on the name than the book she was reading.

Pittsburgh Railways operated trolley cars throughout the city, connecting neighborhoods with convenient public transit: the 75 line, East Liberty-Wilkinsburg, would have been the prominent trolley line for the Shadyside neighborhood.