True love is like a pair of socks

Get into the process of Greg Itahara, an artist from Chicago whose latest creative collaboration is with Swiftwick

Oct 02, 2025

Greg Itahara is an artist, but – to be very clear – he is a runner. I’m talking to him about his “hyper local” sock collaboration with Swiftwick to celebrate Chicago ahead of their marathon next weekend.

A native Chicagoan, Greg has studied there (art at Columbia College), worked there (designer at advertising powerhouse Leo Burnett), and raised a family there. It was when his son was born that he started running, to counteract the new sedentary life of a stay-at-home dad.

After twenty years, Greg suffered burnout. After starting from the bottom rung of the ad agency, he worked his way up to the point that he “felt like just another commodity.” He’d reached his goal and the rewards there were good, but they weren’t enough. He was working hard but felt like his creativity was stifled.

He ran occasionally during this time, but it was just fitting in exercise when he could. It was nothing serious. Running was a normal thing to do. After all, he’d grown up with a father who showed Greg his black post-marathon toenails.

Running vs Creativity

When he “decided to get into a healthier space physically and mentally,” after trading advertising for family, he moved up from 5Ks to a half-marathon before tackling his hometown marathon with a couple of friends. Five Chicago Marathons later, and Greg has retired from marathoning (“I wasn’t a spring chicken when I started!”), and instead runs for his health – both physical and mental, like how he started – and his creative life has blossomed.

“I’m almost getting the excitement and fulfillment as I did through running with my creations for my art for runners. It’s almost the same but I don’t have to go out and do anything physical. It’s more mental.”

I notice this handover of effort and focus in someone’s life – between family, work, and running – more and more frequently. It makes sense, doesn’t it, that you can only burn the candle at two ends. Try burning that candle from a third and there’s a collapse.

Relieved of the intensity of marathon training schedules, Greg found his creative spirit coming forth once again. He was working heavily with the Chicago Area Runners Association, performing freelance graphic design of banners, logos, race bibs, whatever, when someone suggested he post his work on Instagram.

“I started painting my shoes, and posting that for fun, and the ball started rolling.”

That ball was pushed by 2016 Olympic 800m bronze medalist Clayton Murphy when he messaged Greg on Instagram to create some custom-painted gear for him. That social media exposure led to work with everyone from local run clubs all the way to Nike and other top athletes. Greg was a hot commodity once again, but a commodity nonetheless.

The understandably popular hot dog design that Greg Itahara created for Nike in 2021 for the Chicago Marathon. Yeah, I love a glizzy.

Greg’s relationship with social media and the external pressures of publicizing his art is a familiar one. He hates it. He had already deactivated his Facebook when Instagram was suggested to him, and he deleted his Instagram a couple of times when the dread of having to think about the metrics and the perfect time to post just drained him.

“I’m a very introverted person. I can talk forever when it comes to graphic design or running, but if you put me in a room with a whole bunch of random people, I can’t take small talk. After a while, my anxiety because of Instagram and everyone looking at my stuff got to me, and I shut everything down.”

After the second time, Greg realized he wasn’t getting any work, so he returned, and demand was greater than ever. This time, however, he understood that this had to be for his own entertainment.

“I just want to do stuff that’s different.”

Chicago, you’re the inspiration

How could he stand out from artists? Greg’s knowledge of every part of Chicago is what’s set him apart. From living and working all over the Windy City, he understands what makes it tick.

“My first big hyper local was with Nike. Chicago was the first World Major Marathon to come back, so Nike asked me to make a collection, and it was only sold at the North Michigan Avenue store, and my first illustration was a hot dog.”

It sold out immediately, and that tracks. My number one cultural touchpoint in a new city is food, and I know I share that with so many others who love to travel and immerse themselves in other cultures. On my early morning runs in a new city, I’m also scoping out the hottest coffee shops before anyone else is awake, and seeing how far it is on foot to that restaurant I heard about.

When I think of Chicago – a city that I’ve never visited – I think about pickle-laden Chicago dogs at a Cubs game and deep dish pizzas on red checkered tablecloths. Whatever dulls the pain of not getting a reservation at Alinea.

“I like to call it ‘Hyper Local.’ A lot of [visitors] are more likely to recognize landmarks or foods. As a Chicagoan, I love to eat, and what’s more synonymous with Chicago than deep dish?”

“I wanted to elevate it. Instead of just having a running pizza, I wanted something that hits home with a runner. I wanted some sort of connection on a human level – more than just a quirky illustration on a sock. I wanted a tangible time capsule for someone to take back with them. Reliving my marathon days, after 20 miles you gotta dig deep, so you have dig deeper than the deep dish.”

My second cultural touchpoint when visiting a city is a cool souvenir. Why not a sock?

The Dig Deeper sock collaboration between Greg Itahara and Swiftwick, with some delicious deep dish

Do you even think about your socks?

While my everyday sock drawer is neither dull nor empty, the perfect running socks were the last piece of my running wardrobe that I optimised a few years ago. Shoes were first, of course, (Brooks and Hylo) then I searched for the most comfortable shirts (whatever’s nearby) and shorts (Janji), then you will probably think about other accessories like a hat (Fractel) and glasses (Oakley). Then you’ll upgrade all of those at least once before you think about your socks. How much could a $20 pair of socks help, anyway?

Swiftwick kindly sent me a spiel about the moisture-wicking capabilities of their socks that hug the contours of your feet, but also a lifetime guarantee (?!) on the socks’ durability, which gives their claim of creating the “greatest sock on earth” a lot more credibility. I’m a huge fan of companies putting their money where their mouths are.

I prefer putting food where my mouth is, though, so I was intrigued about the other Chicagoan culinary possibilities for these socks. Greg had informed me about pizza puffs and breaded steak sandwiches also originating in his hometown during our chat, so why not an Italian beef sandwich? The Bear is one of the most popular Chicago exports, after all.

“Trying to draw Italian beef on a sock, using pixels… it’s going to come out like chutney,” he laughs.
“There are other socks that do full printing with gradients, but the function of it is not as good as the Swiftwick sock, which is good out of the box for running.”

Printing a design on a t-shirt, poster or even a hat is pretty straightforward, but socks…

“Swiftwick went through the construction and limitations of the sock with me. Because of how it’s made and constructed, and the way it’s stitched, there are constraints, and I have to work within these constraints to make something that still looks freaking dope.”
“I love when I’m presented with a challenge”

Whether it’s running or a new hyper local design, Greg Itahara is ready for the effort, no matter how deep he has to dig.

Running Sucks Running Socks?

Comment below on what designs or collaborations Swiftwick should pursue next to be entered to win a $100 Swiftwick gift card.

You’d better believe that I’m floating Running Sucks Running Socks their way, so if that sounds like something you’d want – let them know in your comment!”

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Raz x