Checkerboard City: Gangster Rap [New City]

Lorena Cupcake Caiazzo/Photo: John Greenfield
By John Greenfield
In a Midwestern town where folks dress conservatively, Chicago bike style icon Lorena Cupcake (her legal middle name) Caiazzo stands out like a handful of Skittles scattered across the Wall Street Journal. Easily spotted by her candy-colored outfits, rainbow-and-lollipops tattoo and messenger bag emblazoned “Cupcake Gangster,” she’s also an astute commentator on the local cycling, drinking and foodie scenes via her frequently updated, often hilarious Twitter feed, @lorenacupcake.
But Caiazzo, twenty-five, is far from just a hipster gadfly. A frequent participant and volunteer at “alleycats,” underground messenger-style checkpoint races, she runs the bike event Twitter calendar @chicagoholdup and helps stage the annual Bicycle Film Festival. Last year she and a few other petite fixed-gear enthusiasts formed Tiny Fix, a bike gang especially for women under five-foot-two-inches, which organizes bar nights, dance parties and now their first alleycat. The Tiny Fix Ace Race happens Saturday, May 26–visit for details. 


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