1999 Ryder Cup fashion flashback: What were they thinking? When Team USA wore the worst shirts ever

The Ryder Cup is here. 2025 promises to be an incredible sports spectacle played out over three intense days in New York at Bethpage Black. The Europeans have an incredible team and will look to beat the Americans on their home turf.

Both teams have had their fair share of fashion disasters over the years, but one specific item of clothing stands out and by far was the worst fashion disaster in the history of the Ryder Cup.

Fashion isn’t for everyone and golfers have been known to wear some ugly items on the course. The Ryder Cup is no different. Europe has had some awful outfits over the years, but the Americans take the cake in the horrendous fashion department. One year sticks out over all of the rest...

The 1999 Shirt disaster

The 1999 Ryder Cup saw a significant uniform mishap for Team USA. The “Battle of Brookline” went down in history as a win for Team USA, but it wasn’t the country’s finest moment due to what happened on the course.

Before we get to Justin Leonard’s putt and the aftermath, we have to take a look at what some have described them as the tackiest and most distracting clothes ever to be seen on a golf course. “I threw it in the fireplace over Christmas and burned it,” Tiger Woods told ESPN. “It was sooo ugly. It provided more warmth for the house.”

Surprisingly, the shirt displayed above was auctioned off at almost $4,000 in 2018. “I don’t think it’s going to get back into the rotation,” Justin Leonard told ESPN. “We will never wear any of those things again.”

Despite the fashion disaster, Team USA will go down in history for winning the “Battle of Brookline” thanks to Leonard’s 45-foot birdie putt on the 17th hole in his singles match against José María Olazabal.

The U.S. players and spectators were critized for their behavior when they celebrated the putt before Olazabal had putted his attempt to tie the hole. The scene on the 17th was a joyous one for Team USA players and fans, but not a proud moment by golf standards due to he unruly behavior. The 1999 Ryder Cup uniforms will likely be remembered as one of the most unfortunate fashion choices in the tournament’s history.