BROOKLINE, : US Ryder Cup team member Justin Leonard celebrates his putt against Jose Maria Olazabal of Spain on the 17th hole that clinched the victory for the US in the 33rd Ryder Cup 26 September, 1999 at The Country Club in Brookline, Massachusetts. (ELECTRONIC IMAGE) AFP PHOTO/JEFF HAYNES (Photo credit should read JEFF HAYNES/AFP via Getty Images)
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Since the days of Walter Hagen and his captaincy in the 1920s, the Ryder Cup has been as much about pushing the boundaries of golf fashion as it has about competition. That said, a few years stand out for producing some truly unforgettable fashion nightmares.
1999 – A Frame Job
The infamous “miracle/meltdown at Brookline is remembered for the United States’ dramatic Sunday singles comeback, but also for one of the worst uniforms in golf history.
The late 1990s style leaned toward baggy pants with cuffs or pleats, oversized shirts with long sleeves, and chunky belts with metal accents. But the shirts chosen by Captain Ben Crenshaw took things to another level.
The polos were excessively baggy, in a brown-and-burgundy color scheme, decorated with giant picture frames containing scenes from past Ryder Cups. Floppy collars and cuffed sleeves made them look more like pajama tops than uniforms. Long considered the ugliest outfit in Ryder Cup history, one of the polos still sold for nearly $4,000 in 2018.
LOUISVILLE, KY – SEPTEMBER 19: Phil Mickelson and Anthony Kim of the USA team celebrate on the ninth green during the afternoon four-ball matches on day one of the 2008 Ryder Cup at Valhalla Golf Club on September 19, 2008 in Louisville, Kentucky. (Photo by Ross Kinnaird/Getty Images)
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2008 – Animated in Argyle
Boo Weekley’s famous “Happy Gilmore” moment, riding his driver down the fairway at Valhalla Golf Club in Louisville, was one of the highlights of the 2008 Ryder Cup. But earlier that week, the U.S. team debuted another lowlight: the argyle polo.
Argyle was trendy in the late 2000s, usually reserved for sweaters and vests. But the Americans wore a stark white polo with oversized navy diamonds running vertically down the right side. Paired with Anthony Kim’s oversized “AK” belt buckle, the look was more cartoonish than classic.
Still, the U.S. cruised to a 16½–11½ victory, proving that sometimes ugly golf shirts don’t hurt.
ROME, ITALY – OCTOBER 01: Luke Donald, Captain of Team Europe, and players of Team Europe pose with the Ryder Cup trophy following victory with a 16 and a half to 11 and a half win following during the 2023 Ryder Cup at Marco Simone Golf Club on October 01, 2023 in Rome, Italy. (Photo by Andrew Redington/Getty Images)
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2023 – Ridiculous in Rome
Despite being played in Rome, and despite Europe’s partnership with luxury Italian clothier Loro Piana, known for its refined cashmere, wool, and linen, the European team’s attire fell flat.
The polos were boxy and unathletic in fit, with an uninspired color-blocked design of pale blue with white shoulders, paired with matching hats. Even the fittest players looked weighed down by the bland design.
Still, Team Europe had the last laugh, winning the Ryder Cup comfortably in their baby-blue-and-white polos and matching hats.
The ugliest uniform tends to steal the show with a correlation between bad looks and good play. Ralph Lauren continues to outfit the American side, this year promising bold geometric patterns, micro logo patterns and large color streaks on player’s tops. In addition, there is a limited edition Ralph Lauren Ryder Cup bomber jacket that is sure to make a worst of list. Loro Piana is back supporting the European team but at this time no announcements have been made as to their uniform.
Source: https://www.forbes.com/sites/break80/2025/09/22/could-this-ryder-cup-produce-the-worst-team-attire/
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