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Windy City Wool

Chicago’s Tweed Ride is a Bloody Good Show

By John Greenfield
Photography by Don Sorsa

Kentucky Derby Day in Chicago, and a pair of southern belles in floppy derby hats are staggering tipsily on high heels from the Metra commuter rail station at Ashland and Cortland. Just west, forty bicyclists, nattily attired in vintage woolen formal wear and mounted on English steeds, combine alternative transportation, fashion and alcohol in a far more dignified manner.
It’s Winston’s Tweed Ride, a tour of former speakeasies that celebrates booze, bicycles and Brits, hosted by the group British Bicycles of Chicago. The jaunt was inspired by January’s Tweed Run in London, where dozens of fixed-gear and single-speed enthusiasts donned dashing duds for a leisurely pedal from Saville Row, famous for its traditional “bespoke” custom clothing.