Playing Dress Up: Time Travel in Tweed

Halloween is a great time to experiment with all your fashion fantasies. But it isn't the only time adults can wear dress up.

I love love love the idea of Tweed Run. They bill themselves as 'A metropolitan bicycle ride with a bit of style.' Which means participants dress in 1920s, '30s, and '40s tweed togs and show up for a bike ride.

The event began in London, started by two transplanted Canadians, Ted Young-Ing and Jacqui Shannon, in January 2009. "Teddy had been to Edinburgh and bought a bunch of plus-fours [a version of knickerbockers] because he thought they were cool," Jacqui told me, but got back to London to discover no one wore them. Because they were both members of a cycling club, they decided to start a "club run" – British version of group bike ride.

Another perk to dressing up for the event: Most Dashing Dame and Most Dapper Chap prizes, which included a Huntsman Savile Row fitting for men. Women won a Pashley bicycle, which is "like riding an armchair," Jacqui laughs, adding, "We were lucky enough this year to attract Ralph Lauren so we were able to bring the event to NYC on Oct. 15, another in London on Nov. 26 (they did one in April), and Tokyo in the spring." The Rugby Ralph Lauren connection made the prizes $500 gift certificates – not too shabby!

I asked her about the ethos behind the ongoing event. She said:

Because dressing well and being polite and a nice person is great. Because tweed is cool. Because cycling should be something not only enjoyed and viable by those in Lycra — and mostly because its FUN."

I couldn't agree more; my riding figures prominently in much of my writing: from kindness to brownies in the road. Plus, bikes are featured prominently in many fashion ads these days — obviously a must-have accessory.

So who comes all dressed up? Jacqui responded enthusiastically:

We're lucky to have the highest female participation of any cycle event in London. We have a verifiable 30+% of women participants ranging from 8 to 50+. As the female producer of the event, I am super proud of that."

I can't help but wonder if women especially like the dress-up aspect, but at just 30%, obviously men like it too. A report in the NY Observer covering the event in NYC included this stylish and savvy quote:

I'm always wearing a suit," Mr. Coleman said. "I love to see women and men dress up to go to work. You hear people in suits say, 'I'm going to change into something more comfortable,' but, for me, dressing up is just as comfortable as wearing pajamas."

My friends Carole and Emilio Delgado decided to join in (wish I'd been there!) – and I'm not surprised. Coleman's quote is probably true for Carole — she has style coming out her fingertips; she scours vintage shops for stylish togs and is always wearing something inventive and enviable.

"Carole certainly was the star of Tweed Run NYC, that's for sure!" says Jacqui. "She has the style. Did you know she brought her own teacup? Truly in Tweed Run spirit."

"I love details," Carole says (the teacup went in her basket while biking). "When I looked through the London Tweed Run gallery, I'd noticed a very distinguished-looking man holding a proper teacup; they did have teacups there but only modern ones." Yet she didn't win Most Dashing Dame. "I think you have to be in the reproductive hormone category to win a prize," she laughed.

Emilio (aka Luis on Sesame Street for years, in case you didn't recognize him) is pretty stylish, too. He's a guest singer with a retro lounge orchestra called Pink Martini, and will be seen in Sarasota, Florida in spring 2012 as Claudius in Hamlet at the Asolo theater. Sarasota's a great biking town, so will he bike there, and dressed up? "Why not! They had summer riding clothes in the '20s and '30s."

"Sometimes you have to go first in fashion, to give others permission to follow," Carole sagely observes. The couple bought vintage bikes on Ebay for the event. "The Tweed Run bought us back to biking," she says happily.

Does it inspire you to want to bike? In tweeds? Maybe a Tweed Run will come to your neck of the woods.