Virgil Abloh has become one of the biggest designers in the world, but it didn’t happen overnight. The Rockford native began working at an architecture firm in Chicago after receiving his Master of Architecture degree at the Illinois Institute of Technology (IIT) in 2006. Around this time, Virgil was also delving into other passions: writing for the fashion/design blog The Brilliance!, occasionally DJing at a local sushi spot, and hosting pop-up shops for tees designed by him and his friends under the collective name Fort Home. It was while working on t-shirts at a Chicago print shop that Virgil connected with Kanye West and the rest is history… more or less.

The mid 2000s was a period of growth for Virgil, as well as for Chicago’s streetwear scene. Wicker Park was starting to become Chicago’s version of Fairfax with boutiques like Saint Alfred opening up down Milwaukee Avenue.

Virgil Abloh modeling for Saint Alfred, circa 2006.

In a 2006 video, Virgil gives a tour of the neighborhood, guiding the viewer to his favorite shops such as Hejfina (RIP), Quimby’s Bookstore, Uprise Skateshop, and the aforementioned Saint Alfred. Virgil would eventually open up his own retail space in the neighborhood, RSVP Gallery, with fellow designer Don C. Step into the time machine by watching the video below, courtesy of the now defunct Midwestern Goodness.