Mid-ride. Dawn Petty, (front, right), one of the organizers, wore lace gloves that could her a good grip.

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Bernard Lambert was dressed too smart. He’s been wearing vintage clothes for at least 15 years. When John Petty, the founder of the Philadelphia chapter of Dandies and Quaintrelles, a local group for vintage lovers, walked by him, he couldn’t help but mention how Lambert pops.

Lambert wore a red stripe seersucker blazer with blue stripe seersucker pants. A patriotic picnic blanket pattern hankie brought the outfit together, as did a multicolored diagonally striped tie. Lambert later won the Dandiest Dandy award. He told us he picked the outfit to work with his shoes, and he picked shoes that would be okay to bike in.

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Philadelphia’s first-ever Seersucker Bike Ride and Social brought out roughly 30 participants to ride while dressed to the nines. Many vintage fans described it as the summertime spin on the autumnal Tweed Ride.

The premise for both events is pretty much the same— gather a group under the throwback theme and have an easygoing ride around the city and a picnic. The Tweed Ride has an afterparty at a bar. The Seersucker Ride culminates in the picnic with badminton and croquet. John, who is heavily involved in both the cycling and vintage worlds in Philly, says he and wife Dawn Petty were inspired by DC’s Seersucker Ride.

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“When my wife and I got into vintage, one of the things that struck us was whenever we were with a number of people in the vintage community, we were always out of town,” said John. They knew there was a community out there in the city, but they weren’t involved, but they got “plugged in,” they were with it. Still, seersucker rides were something they had to go elsewhere for. “We both agreed, perhaps we should have something here so we won’t have to travel all the time,” said John. They spent the last seven months or so planning this first one, which they hope to make an annual thing.

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Credit: Jenna Eason/Billy Penn

John thinks participants are more willing to get on board with this kind of themed ride than others. “Frequently when you have these events, you have people rebelling just for the sake of [it.] ‘I know it’s supposed to be all white, but I’m wearing black,’” he said. “But with the vintage thing, people tend to buy in and tend to get with the flow.

They started in Old City and cut across the city through Rittenhouse Square. The group took a break in Markwood Playground in Fitler Square. This was a moment for water, chit chat and 1920s jazz. Afterwards, they made their way back across the city for the social at Fishtown’s Penn Treaty Park. The day was quite hot, but ice cream was available from (of course) Franklin Fountain.

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Friends Rachel Vause and Emily Shartrand sat down at the social for one of those picnics that, to anyone who’s not a vintage enthusiast, might look storybook. Vause’s curls were still there after the seven miles. “Tresemme No. 4 hairspray holds anything,” she said. They were two of many who rode the whole way in heels. 

“Actually, you can kind of wedge the heel right in behind your pedal and push. I think it’s easier than if you have a completely flat pedal because that could slip,” said Shartrand. “So I haven’t found the biking hard at all Definitely, the holding head gear down is the harder part.”

Among the coolest things about a ride like this are the faces people make and questions they have when they pass by. When more than two dozen cross a corner in period dress, people stop and ask what they’re doing, tell them they look great once they know.

“‘Is there something that I should know? Like, did I just travel back in time?’ The reactions are pretty funny,” said rider Bridget Law, who’s attended seersucker rides in other cities. “It’s a whole lot of fun.”

Cassie Owens is a reporter/curator for BillyPenn.com. She was assistant editor at Next City and has contributed to Philadelphia City Paper, Metro, the Jewish Daily Forward, The Islamic...