Question: how do you dress for riding a bike?

Today I’m going to answer a question I get asked a lot.

Tanya emailed me this:

“I don’t wanna have to cart my office clothes with me on my bike, nor is my body fit for the great outdoors in tight lycra! Help!”

I hear you Tanya. I ride in what I’m wearing for the day. No need to complicate life with changes of clothes…seriously. Here are some tricks I employ:

1. Embrace dressy shorts. I love these ones below from Sass and Bide. I buy them a size or two too big.


2. Yes, you can wear heels. I do all the time. Just buy ones that support your foot in some way – eg boots or ones with straps over the arch of the foot and around the ankle. The heels below are from All Saints – they’re like a laced-up desert boot. When riding with heels you do need to be careful you don’t slip…but this extra psychological pressure actually makes for some nice hyper-aware and aligned riding. What about wedges? They don’t work, really. I’ll scoot down the road in them, but there’s no grip to be found. Save them for walking.

Here’s Lucy from Love at 1st Sight (Lucy builds single speeds in Bondi, if you’re interested) wearing booties:


3. Short dresses with stockings in winter are great. A scarf you can tie to your bag is good too. I rode to this red carpet event in the city back in winter (much to the shock of publicists), wearing this:


Boots are good. When riding in skirts or dresses, I just tuck the fabric under me and try to keep seated.  I think this is quite a clever way to deal with skirts:

Photo: Bojun Chiswell / as seen in Treadlie magazine
Photo: Bojun Chiswell / as seen in Treadlie magazine

4. Find yourself a great commuter handbag. I’m always on the lookout. Sass and Bide have done a great two-strap satchel.  The one I carry in the shot below is a Country Road leather satchel that slings over my shoulder. I can fit my Macbook in it. And my lunch.

Sarah+Wilson+Oprah+Winfrey+Visits+Australia+L Question: how do you dress for riding a bike?

Here’s a close up of the bag (as a hipstaprint, of course):

My HipstaPrint 0

5. Invest in T-back singlets and T-back bras. I find these allow a lot of movement and mean you don’t get fabric build-up under the arms, which collects sweat. Knowwhatimean? I buy simple, cheap T-backs from Target. American Apparel singlets are good.

6. Buy long tops…so they cover things at the back. Bum crack in drivers’ faces ain’t going to help your cause.

7. Over time, gradually, shift your wardrobe to be all about soft, flowy, stretchy layers. I think this girl does it beautifully:

Photo: Martha Williams / as seen in Treadlie magazine
Photo: Martha Williams / as seen in Treadlie magazine

I’ll do a second post with more hot looks and suggestions. Please send me pics of yourself if you’re a rider…let’s inspire each other….

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