If you look at images of Tiger Woods from the 1990s, you’ll notice that everything he wore was a little big on him. This was mostly the work of his father, Earl, who sized up himself, leaving Tiger swimming in hand-me-downs early on in his amateur career.
I’ve had the pleasure of getting to know Tiger through the years, and one thing I can tell you about his style that won’t surprise you is that he doesn’t love change. Who could blame him—whatever he had going on was working. His comfort level with oversized clothes continued into the peak years of his dominance in majors with Tiger emulating Michael Jordan’s full-cut trouser style, hence all of these oversized pants they both wore in those years.
Tiger’s physique has always resembled that of a Greek god with wide shoulders and a very narrow waist. His mother, Kultida, told him early on that he needed to match his belt to his shoes and his hat to his shoes. A lot of golfers think that, but it’s really not the case.
Eventually, Tiger’s fits began to flatter his frame more. He lost the pleats and tightened the shirts. Comparing the earliest images of Tiger on the golf course with the latest images of him in his new label, Sun Day Red, reveals a decades-long evolution that you might have missed if those red shirts were the only ones on your radar. Tiger may look more muscular now than he ever has, but the clothing he’s wearing does his physique far more justice. Now he looks more like the superhero that he has been for 30 years.
Remember, it’s not really what you wear as much as it is how you wear it. If you have any questions about that, take a look at Adam Scott. You can buy his entire outfit on any given day at UNIQLO for a hundred bucks and get change back. It’s not about how much money you spend or about what fancy labels you buy; it’s about wearing the correct size, wearing the correct colors, and putting them all together. If you can do that, you can get away with a multitude of sins. That, or be Tiger Woods.
AT HOME, 1994 
Photograph by Dom Furore
Shirts that have a knit collar are going to curl during the course of a round; there’s no stopping it. This is also a raglan-sleeve shirt—you can see the diagonal seams—so it doesn’t emphasize how oversized it is because of the way it’s cut. This was the era before every golf shirt was made out of synthetic material. Tiger’s polo here is likely 100 percent cotton, and if it belonged to his dad, it got softer through the years.
1994 U.S. AMATEUR 
PGA TOUR Archive
This might be one of Tiger’s most iconic looks, not just because the trophy pairs with it nicely but because we get to see some personality. He wore a straw hat like this a few times in his amateur days, but in the pantheon of his career it’s a rare sight. The clothes are still oversized on his trim frame, but there’s enough excitement in the way he put it together that this is an occasion where it really worked.
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Tiger started working with Butch Harmon in the early 1990s, and Butch had an investment in a belt company, a small boutique brand called the House of Fleming in Atlanta. Butch gave Tiger some of these cool belts, and this is one of them.
2000 WITH EARL 
Chris Stanford
Because of his aversion to change, even a decade after we first saw him emerge in Earl’s hand-me-downs, Tiger continued to wear oversized polo cuts.
2004 
Darren Carroll
The cut of his trousers is very generous. If they fit him better through the hip, his belt wouldn’t have to work so hard. It’s another example of a silhouette gone wrong. You might think these wide-leg trousers would allow more freedom of movement, but that’s not the case. Watch the Summer Olympics. Do you see guys running the 100-yard dash in oversized running shorts? I don’t think so.
2007 
Walter Iooss
We all know that Tiger’s power color is red—one thing his mother definitely got right in terms of style advice—but this all-black look is one of his finest. It’s a perfect example of how much Tiger looks like a superhero when his clothes fit him. These pants aren’t slim fit, but they fall straight as opposed to the billowing fabric of previous years.
2011 
Robert Laberge
Now he’s starting to get refined. This shirt is a good fit with the shoulder seam kissing the shoulder blade.
This is about the time Tiger starts to understand. Nike buys into it, too. Nike was so intimidated with Tiger in the beginning. No one put their foot down and said, “Stop wearing ridiculously oversized clothes.” Had he worn a black glove with this outfit, it could have looked cool.
2013 
Sam Greenwood
This is a good example of Tiger wanting a golf shoe that looked and felt like the ones that he loved to work out in. The TW ’13 was so popular, Nike brought it back last year to much success. Even as the golf-sneaker market evolves and expands, the TW ’13 endures as an all-around brilliant golf shoe
2024 
Michael Owens
I think the idea of channeling Tiger’s power color within the brand’s name, Sun Day Red, is a good idea. The execution we’ll have to judge over time, but taking a look at what he wore to Riviera this year, these are garments that fit him, and I’m impressed with that. It’s the perfect culmination of Tiger’s gradual movement toward a more tailored look as the years have passed. Tiger earns bonus points here for a brave monochromatic look.
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This article was originally published on golfdigest.com
