Gangster rap: an interview with bike style icon Lorena Cupcake

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[This piece also appeared in Checkerboard City, John’s weekly transportation column in Newcity magazine, which hits the streets in print on Wednesday evenings.]

In a Midwestern town where folks dress conservatively, 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.

But Caiazzo, 25, 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 5’2”, which organizes bar nights, dance parties and now their first alleycat, last weekend’s Tiny Fix Ace Race.

I recently caught up with Caiazzo, fresh off her day job as a bank teller, over $3 cheeseburgers at the Blue Frog, a messenger bar at 676 N. LaSalle in River North. She gave me the skinny on Tiny Fix, the upcoming race, and the things she loves and hates about biking in Chicago.

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