Are Tiger Woods’ Sun Day Red golf shoes worth the hype? Full Pioneer Cypress review

Meticulously crafted for serious players, the Pioneer Cypress delivers premium style, firm support, and iconic Tiger Woods DNA for golfers who demand the very best.

Tiger Woods. We’ve seen him lace up in more legendary golf shoes than probably anyone in the history of the sport. Through his years with Nike, he helped design some of the most iconic models ever, most famously, the Nike TW series. For me, it was the TW 13 that truly set the standard; the pair every young golfer (myself included) wanted to wear to feel just a touch closer to Tiger’s magic. Now, after a stint in FootJoy’s following his comeback, Tiger is back with a new chapter: the Sun Day Red Pioneer Cypress.

So, can Sun Day Red live up to that storied legacy? Honestly, the Pioneer Cypress feels like what would happen if Nike took its best shot at making one of the best spiked golf shoes, a FootJoy Premiere, blending technical sharpness and tour-ready support with the heritage style and premium leather that are FootJoy’s signatures. It’s a marriage of modern cool and classic tradition.

But here’s the real question: will they be as good as those icons, or even better? With Tiger Woods’ reputation for obsessing over the minute details (he’s walked over 40 million steps on Tour, after all), you know the bar is sky-high. The Sun Day Red Pioneer Cypress doesn’t try to be an “ultra-comfy” sneaker-style trainer; it’s a premium, purpose-built shoe for those who care about quality, performance, and tour-level looks.

So, is it the new benchmark for a Tiger shoe? While it may not feel like the soft Sun Day Red Osprey sneaker, it’s got that unmistakable “built for legends” vibe the moment you lace it up.

Comfort: 3/5

Let’s be real: you don’t slip on the Sun Day Red Pioneer Cypress expecting marshmallow softness underfoot. These shoes are all about that high-performance, tour-ready feel. Yes, they’re on the firmer side, think “built like a sports car” more than “slippers,” but that’s kind of the point. The leather-wrapped padded heel hugs your foot in just the right way, and the lush calfskin lining is a treat (Tiger’s feet are living well, folks).

Breaking them in is a classic case of ‘no pain, no gain’. You’ll need a round or two, but there’s zero drama. Ironically, I had no blisters, just a touch of first-day stiffness that disappears fast. What I thought was a nice touch was the two insole options to fine-tune your ride. Comfort is classic and purposeful, not pillowy, and that’s exactly what some players crave.

Performance: 4/5

Now we’re talking! This is where the Pioneer Cypress starts flexing its Tiger-inspired muscles. That low 6mm heel-to-toe drop was designed with ground force in mind, and you can feel it in your feet stay cranked into the turf and ready for liftoff. Traction is excellent in all conditions; wet grass, fluff, sand traps… You name it, you’re sticking the finish.

But here’s the head-scratcher: why, on one of the most premium shoes in golf, are we still rocking Pulsar soft spikes rather than the serious Tour Flex Pro cleats the pros love on Tour? It’s a good grip, don’t get me wrong, but for this price, I wanted the full Ferrari experience, not just a shiny paint job. Secure fit and solid midsole mean you can swing free, trust your stance, and not worry about a thing.

Durability: 5/5

If you’re dropping big money on a shoe, you want it to last, and the Pioneer Cypress laughs in the face of rough conditions. The full-grain waterproof leather upper is built like a fortress, shrugging off scuffs, stains, and even sideways rain. The plush suede inside keeps things cozy round after round, and even after a few miles, there’s barely a crease. Every stitch screams quality, from the fancy Tiger-stripe embossing to the reinforced eyelets. This is a shoe that will probably look even better after you’ve given it some stories to tell.

Style & Design: 5/5

If there were a green jacket for golf shoe fashion, this one would be making a victory speech. The Pioneer Cypress oozes old-school cool and understated flair. Sunday Red logos pop in all the right places, the heel detail pays homage to Tiger’s greatness, and those classic colorways work with literally anything in your closet, shorts, joggers, trousers, you name it. Even the laces get the luxury treatment with custom eyelets. This shoe is all about confidence and class.

Technology & Features: 4/5

Under the hood, this shoe’s packed with smart design. The Tiger-driven heel-to-toe drop gives you the low, athletic feel he swears by. The 9-cleat setup (plus some feisty little TPU nubs) means you’re stable wherever you swing. Is it waterproof? Of course, it’s ready for UK links or Augusta drizzle. And you get not one but two insoles for dialing in fit and feel. Still, it’s hard not to wish those spikes were the Tour Flex Pro. An easy fix, I know, but this is Tiger’s shoe, after all… shouldn’t it get the Tour spike treatment?

Final Verdict: 21/25

The Sun Day Red Pioneer Cypress isn’t trying to be your everyday comfort shoe; it’s built for players who want to channel a little Tiger and crave premium feel and performance. Sure, you might want more squish if you simply stroll the fairways, but if you dig classic lines, tradition, and feeling absolutely locked in, this shoe’s the real deal. Just don’t expect top-level cuddly comfort; expect stability, style, and leather that might outlast your own golfing career. And hey, if they swap in those premium spikes in a later update, it might just be the closest thing to Tiger’s own magic you’ll ever lace up.

Sun Day Red Pioneer Cypress Golf Shoes

RRP: £228.00 / $250.00

Colorways: Multiple

Sole: Spiked

BOA: No

Waterproof: Yes

Fit: Fits to size