The Wanderer Collective: An Interview With Olivia O'Connor

There are some people who just grab your attention, hold you captivated and leave you wanting more.

The newest inductee into the Wanderer Collective is one of these sparkly souls.

I can't tell you how many hours I've lost stalking causally browsing her blog and Instagram feed, because the girl is just so damn captivating. Her bright shiny vibe and go-getter attitude is inspiring, and as an American now living in Australia, she epitomises the wanderer spirit. And now she's set her sights on changing the world, one hat at a time.

She's sassy.

She's savvy.

She's Olivia O'Connor

Welcome to The Wanderer Collective, Olivia! Tell us a little about yourself, lovely

Thanks for having me, Shanny! I’m an American, living in Sydney and the founder of DontTellSummer (Hats with a Purpose™). Each hat is made to inspire you to do what you would love to do now, rather than waiting for some point in the future. Every time you put on the hat, it’s a declaration to live an authentic, rad life. Whether that’s saying yes to going for a surf that day, or to a dream that’s been sitting in your heart, they are here as a reminder to do what you love, what completely excites you.

Something that I’m really passionate about is young people going for their dreams now, living our truth now and doing what completely excites us now. Because of this, I’ve created a fund for DTS where a portion of every purchase goes to a young person with a big dream.

My hope is that when people wear a hat or are around a friend wearing a hat, they are empowered to have fun and to do what they would absolutely love to do.

I’ve got 15 stamps on my passport, but I left my heart in…


We wanderers have a never-ending supply of interesting stories to tell. What’s the most memorable travel experience that springs to your mind?

I’d have to say riding elephants in Chiang Mai, Thailand.

I went with my family and friend two Christmases ago and it was such a unique experience. Looking back and seeing my parents on elephants felt surreal, I couldn’t stop smiling the entire time. The best part was when we got to go in the water with them. I have this photo from when the elephant came up behind me and put me on its trunk. It is one of the best experiences by far!

What’s one thing you won’t board a plane without? 

My journal. I got it in London during High School and that was my first big International trip. There was something about the journal that I loved and made me feel safe, and so I bring it every time I go on a trip.

Someone got it right when they said… 

"Travel not to find yourself, but to remember who you’ve been all along.” It’s so true!

(I’m not sure who said this but I love it!)

This one time, when travelling, I woke up in… 

The Rip Curl House in North Shore, Oahu.

It was surreal. I was there for my Grandma’s birthday, staying at a hotel with my family, and my friends picked me up to stay with them on the North Shore. By the time we got there, it was dark out and so I wasn’t exactly sure about my surroundings.

I woke up to the sound of the ocean (the house was on the beach!) and to surfers walking around the house. I turned to my friend to ask him where we were and he told me we were at the Rip Curl house. My jaw dropped. I wish I had a girlfriend there to freak out with.

We’ve all crossed some pretty cool shit off our travel bucket lists. What’s your top 3 items of places yet to go?

1 // Greece

2 // Rio De Janeiro

3 // Croatia or Italy

Fast Five:

Instagram or Twitter? Instagram!

Hotel or hostel? Hotel. I love relaxing in cozy beds. I’ve always been like that. I’m the most adventurous person during the day as long as I know that I have a cozy bed to go back to at night.

Best travel tune on your iPod? The Suburbs by Mr. Little Jeans (Arcade Fire cover)

Travel blogger to follow who knows their shit? Dirtbag Darling, The Gear Gal and FiftyTwo Truths (Ya!)

[Awwww, thanks sunshine! *blush*]

Next on my travel itinerary? A trip with my friends to Mykonos!

A final question before we leave you: If you could give one piece of advice to first-time wanderers, what would it be?

Just go! There are always reasons to push it to some point in the future, but when you have that inspired feeling that you’d love to go and travel, go!

Whenever fear comes up for me around this I tell myself, 'You can always go home'. Knowing that makes me feel confident in going for an experience I would love to have.

Bio //

Olivia O’Connor is an American, currently living in Sydney, and founder of DontTellSummer – hats made to inspire you to do what you love.

Through blogging and coaching, she inspires young individuals to go for their dreams now, rather than waiting for some point in the future.

You can check out her rad shiz here, here, and here.

Shanny3 Comments