Surprise, You’re a Winner!

03 Nov

During Bike to Work month last May, the San Francisco Bike Coalition sponsored a Dress Up Challenge. Compared to other bike challenges, like the CLIF 2 Mile Challenge or our local Drive Less Challenge, the Dress Up Challenge was an easy, one-shot deal. Simply photograph yourself with your bike all dressed up for work and post it on the SF Bike Facebook wall. A winner would be selected by random drawing at their Bike to Work Day after work party.

Since I dress up for work and ride my bike to work every day anyway, all I had to do was pick a favorite outfit and convince my husband Dick to get up early and take the photo. I did my best to imitate the natural easy style of Dottie and Tricia’s bike photos on their Let’s Go Ride a Bike blog. It wasn’t easy, since I’ve never been that comfortable in front of the camera (I’m better now). Fortunately, writing the caption was much easier: “Timeless Charm: Pearls, pleats, and polka dotted stockings on Juliett, my Dutch bike.”

So I posted the photo to the SF Bike Facebook wall and then posted it to my own wall with a message asking my friends to join me in the challenge. I don’t know if anyone took the challenge, but the compliments I got were addictive. So for the 15 remaining work days leading up to Bike to Work Day, I posted a dress up photo on Facebook and ignored that little voice that told me that people would think I was vain.

When it was over, my friends asked if I had won, telling me I deserved to win. I explained that it was just a random drawing, and that no, I didn’t win. While I was relieved to not have to plan photo-worthy outfits each day, I wasn’t ready to stop. So I started posting a photo a week on “Fashion Fridays” and Dick regretted he’d ever agreed to take that first photo.

Then I started this blog about my bike fashions and bike adventures and I forgot about the contest that inspired it all until last Saturday when I came home to a couple of packages from the SF Bike Coalition. “You were chosen as our Dress-Up Challenge Winner for 2011!” the letter said, “your enthusiasm for bicycling was inspiring and contagious.” The package was a sweet Nutcase helmet and a top tube sleeve from Rickshaw that happened to match the herringbone mini-bag I had just bought at their warehouse. Awesome! I didn’t take the challenge to win prizes, but surprise gifts are always fun.


For those who missed my Dress-Up Challenge photo series on Facebook, here’s what I wore to work for the two weeks or so leading up to Bike to Work Day last May. Click the thumbnails for high-res photos.

What’s the dressiest outfit you’ve ever worn on a bike?


Posted by on November 3, 2011 in Cycle Fashions


5 responses to “Surprise, You’re a Winner!

  1. Charles

    November 3, 2011 at 10:22 pm

    You are amazing Janet. What an inspiration!

  2. Helena

    November 4, 2011 at 7:26 am

    Janet, that’s so cool! Congrats! You set the gold standard for commute style and grace.

  3. NadiaMac

    November 4, 2011 at 9:07 am

    woohoo, congrats!

  4. Lisa

    November 6, 2011 at 5:23 am

    Love your style!

  5. bicycletravels

    March 4, 2013 at 2:26 am

    I want to have your wardrobe… 🙂


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