Dominate Hills in a Dress - Bike Outfit Ideas

When choosing your outfit for a big dress-up bike ride, I recommend doing a test run.

I'm riding the Anjou Vélo Vintage this June. It's a 33 mile ride through the Loire Valley in France. Everyone dresses up in vintage clothing and rides bikes that were born no more recently than 1987.

Yesterday brought unseasonably warm weather to San Francisco. It was like a little hint of Summer. Perfect conditions to try out my costume for the Vélo Vintage by riding across the Golden Gate Bridge and into the Marin Headlands.

View Going over the Golden Gate and to the top of Hawk Hill in a larger map

Riding through the Presidio, I got a spectacular view of my destination.

Hawk Hill is a favorite spot for San Francisco cyclists. And it's easy to see why. The climb is challenging, but not grueling. And the incredible view of the bay, the bridge, and the city made it easy to ignore my complaining legs.

When I reached the top, I was the only person who had done the climb in a dress. All the other cyclist had on Lycra kits and clip-in shoes. I felt pretty proud of myself for making it on my platform pedals and vintage Ferragamo oxfords.

The descent from Hawk Hill on Conzelman is a one-way road boasting an 18% grade at some points. I'm a huge chicken when it comes to downhills, so I rode on my brakes nearly the whole way down. But the view of the cliffs and the Pacific is incredible.

I'm wearing a vintage Navy Blue Slip, similar to this one. It was super comfortable for biking. Underneath, I have a pair of inexpensive (padded) biking spankies. For these shots, I added my mom's belt from the 80's. I don't recommend doing a big climb with a cinched-waist!

Vintage Ferragamo shoes are notoriously narrow. These are a half-size larger than I normally wear and they feel ever-so-slightly snug across the ball of my foot every time I put them on. However after about 15 minutes, they stretch and are incredibly comfortable. They were excellent for biking in.

Riding the Golden Gate Bridge at dusk is a treat. The crowds have thinned and you can watch the sky turn pink in the setting sun.

After those hills, I was near to bonking. I stopped in the center of the bridge for a snack. I can't imagine a more beautiful spot for a picnic.

One last look at the bridge.

You may have noticed that this bike is neither a single-speed, nor made of bamboo! My road bike was a much  more practical choice for this ride.

Also, I didn't even attempt to do anything clever about my helmet hair. Instead, I wore this pretty, printed handkerchief from Givenchy.