Interview by Irma Gunadi

Photography by Trent Williams


When he’s not up at the crack of dawn riding his bike or managing our Sydney Men’s store, Troy O’Shea can be found handcrafting cycling caps for friends and fans alike under the brand name Troy O’Shea Handmade. We stopped by his Balmain home to chat about turning a pastime into a business and how practice truly makes perfect.

Hi Troy! What inspired you to start making cycling caps?

My wife and I were in San Francisco and I came across this small bike shop that was selling beautiful handmade cycling caps. I’d only ever seen mass-produced ones, so I was really taken aback by the quality and time that had gone into them.

Was there a lot of trial and error involved?

I had never sewn before, so I enrolled in a beginner’s sewing class at Sew Make Create in Chippendale. My first project was actually a cushion! After I finished two classes, I purchased a machine then started making caps. I made countless caps before I actually started selling them.

When do you decide that a cap is “finished”?

I don’t believe that any of my caps are ever really finished. But this is what I find most appealing about making something by hand – it will never be perfect. I think it’s the same for any hobby that you are passionate about, you’re always striving to improve and better yourself.

Do you ever get frustrated when things don’t go as planned?

Occasionally yes, but you always learn something from the mistakes you make. At least, that’s what I tell myself!

Your wife is Japanese, you spend a lot of time in Japan and are fluent in the language. Has the Japanese reputation for beautiful workmanship influenced you in any way?

Absolutely. Living in Japan for almost three years, I quickly recognised the time and dedication that everyone devotes to achieving perfection, which was incredibly impressive and really resonated with me. I try to emulate this in everything I do.

What are you currently working on?

Recently, I’ve been working on some non-cycling related designs modelled off WWII military caps. I’ve also been working with some new materials, like Japanese selvedge denim and heavy canvas.

Name three things that make for the perfect bike ride.

Blue skies, nice scenery and good company!

Troy sells his caps through his Instagram account @troyosheahandmade and online at