The Story Behind Tiger Woods' New Sun Day Red Golf Sneaker, The Pioneer Cypress

Tiger Woods shook the golf world when he announced his departure from Nike. The man who spent nearly 30 years at the brand had suddenly left, leaving many to wonder where he would take his talents. Our questions were answered shortly after, as it was announced that Tiger would start Sun Day Red, a golf apparel line made in partnership with TaylorMade.

While the label has been pumping out apparel since May 2024, it will soon introduce its first performance golf sneaker—the Sun Day Red Pioneer Cypress.

Embodying Tiger’s legacy and passion for perfection, the shoe’s development involved over 20 prototypes, with Tiger working closely with designers Charley Hudak and Tyler Pinkos to refine every detail. Their mission was clear: create a product that draws from heritage golf sneakers and combines that design language with cutting-edge performance features. From the geometry of the outsole—influenced by Tiger’s swing mechanics—to the waxed laces that address a typical golfer's frustration, every element of the shoe reflects Tiger’s insights and exacting standards.

In an exclusive interview, Hudak and Pinkos provide a behind-the-scenes look at the making of the Pioneer Cypress. From the challenges of meeting Tiger’s exacting standards to the inspiration behind the shoe’s standout features, they share insights into how Sun Day Red is poised to carve out a unique identity in the competitive world of golf footwear.

Images via Garret Byrum

With this being Tiger’s first sneaker outside of Nike, how does Sun Day Red plan to differentiate itself in the competitive golf footwear market?

Tiger is our north star and performance is core to Tiger. Performance and innovation will always be key tenants to our design ethos. Obviously, we all want to look good while we perform, but to enhance performance is the goal and we see footwear as equipment, a tool for those that desire to improve and become great.

Tiger’s involvement in the design process is emphasized throughout the press release. Can you share a specific example where his feedback directly influenced a significant design or performance element?

It’s pretty safe to say that every aspect of the footwear was influenced by Tiger. A lot of his insights were performance related, but he has an impeccable taste level as well. One instance in particular was the transition during the swing that allowed him to “get on point.” This influenced the geometry of the outsole perimeter.

With nearly 20 prototypes tested, what were some of the biggest challenges in meeting Tiger’s exacting standards?

The greatest challenge, like with any project, is time and communication. It was a process and the more we responded to his requests, the more trust we gained. There was no silver bullet, but we were all committed to the idea of hard work, dedication and continuous improvement.

The Pioneer Cypress blends classic golf shoe aesthetics with modern performance features. How did you strike the balance between tradition and innovation in the design process?

Once we nailed down Tiger’s desire to have a more traditional, heritage aesthetic we worked tirelessly on the problem statement to provide him with that aesthetic, while not letting that inhibit our quest to build the highest performing golf shoe to meet not only his demands, but those desiring to advance their game.

Stability, comfort, and ground feel are critical features highlighted in the Pioneer Cypress. Can you describe how the spike design achieves the “tiger-like claw effect” and its impact on performance?

The objective was to create a traction plate that would perform under any weather condition regardless of terrain while also giving him, and anyone else wearing this shoe the confidence to perform without compromise. He was also extremely cognizant of preserving the integrity of the greens so as to not impact other golfer’s experience. It’s a fine balance, but we understood the mission and respected all of his desires.

Can you elaborate on the symbolism behind the Tiger Stripe deboss pattern and how it reflects Tiger Woods’ persona?

Tiger is a fierce competitor and the parallels to the animal have been synonymous with the way he plays the game. We added the deboss pattern as a tribute and believe it’s fairly iconic that will also symbolize greatness.

Tiger’s motivational expressions, “Do the work” and “Put in the time,” are hidden in the insoles. How did his philosophy influence the broader design and messaging of the shoe?

Everyone working on this project was inspired by Tiger’s work ethic and relentless pursuit of greatness. We took his same mentality and tried our best to mirror that by building him the best product we possibly could. Tiger deserves the best.

The waxed polyester blend laces seem like a small detail, but they solve a common golfer frustration. How important are these small design choices in creating a high-performance shoe?

Man, that was a moment. At the Genesis in February we saw him first hand fiddling with his laces and immediately knew we had to make an adjustment. And sure enough, we got the feedback and made the change. It was just one more example of things that we learned along the way. Every stone needs to be turned over to make great product.

What was the inspiration behind the red tread plate and other red accents on the Black/Red and White/Red colors?

Historically, Tiger kept things pretty simple and classic. The idea of adding some hits of color actually came from his son Charlie. The red bottom plate gave us the opportunity to make a statement without distraction.

What was the most rewarding aspect of working on the Pioneer Cypress, both as a design team and as a collaborative effort with Tiger?

The most rewarding part of the effort was the process. The long flights to Asia, the grueling days at the factory, the countless hours testing the product, the late night video calls, etc. The journey being the destination. Looking back, we will cherish those moments and it will fuel us for years to come.

Sun Day Red is launching with such a premium product. What does the Pioneer Cypress signify about the brand’s vision and goals for the future of golf footwear?

We believe that we are just getting started and to be able to lean on a guy like Tiger Woods puts us in a very good place today, tomorrow and the years to come. It’s a mindset and he’s our muse. To say the future looks bright would be an understatement, at least in our eyes.

Is there a feature or design detail in the Pioneer Cypress that you believe will particularly surprise or delight customers?

We believe that the sum of all the parts will surprise the customer. We put love, sweat and tears into every detail of this shoe. But beauty is in the eye of the beholder you know. We think there is enough here for anyone and everyone to find something delightful. That said, one thing that stood out to some of our early fit and wear testers was the idea of out of box comfort and that they said it kept getting better.

With the December 4 release coinciding with Tiger’s Hero World Challenge, how do you anticipate this launch will resonate with both Tiger’s fans and the broader golf community?

We would imagine that the Tiger fanatics will be extremely excited to get a piece of history with his first footwear launch. A shoe built for Tiger by Tiger. And, we also think that any golfer looking to improve their game will be excited to participate as well. Can you imagine not wanting to wear golf shoes that Tiger helped create?

Finally, anything you would like to tell the world about the silhouette that we haven’t touched on?

Just wanted to share that this was truly a labor of love. The footwear product creation team including Tiger worked extremely hard to bring you a product that we hope you will love, for a game that you love and it was all inspired by an athlete, who at one moment or another, has graced us with moments in time that we all love.

Download the Sole Retriever mobile app to stay updated on the latest releases, raffles, news, and more in the sneaker and streetwear world.

Nicholas Vlahos

Sneakerhead from South Florida who turned his passion into a career. When not writing for Sole Retriever, I enjoy watching films and discovering music. Follow me on Letterboxd @nickvlah For tips, reviews, or any shoes in a size 13, email nick@soleretriever.com