Joshua Goldman
Joshua Goldman
min read · September 3, 2025 · Entertainment

Taylor Fritz's Upside Down Headband: A Fashion Faux Pas at the US Open

Taylor Fritz inadvertently put his headband on upside down before heading out on court

TENNIS TROUBLE: Taylor Fritz's Epic Wardrobe Blunder Leaves Fans in Stitches and His Girlfriend Cringing

In a shocking display of fashion faux pas, American tennis star Taylor Fritz's headband sponsor may have just gotten a whole lot more attention than they bargained for after the young player accidentally wore his Hugo Boss headband upside down during his high-stakes US Open quarterfinal match against Novak Djokovic on Tuesday night. The California native, seeded No 4 at Flushing Meadows, was gearing up for one of the biggest nights of his career as he took to the Arthur Ashe court, but little did he know that his wardrobe would become a laughing stock instead.

As Fritz made his way into the locker room before the match, his team and coaches likely breathed a sigh of relief knowing their star player had finally made it to the quarterfinals. After all, it's not every day you get to compete on the hallowed grounds of Arthur Ashe Stadium in front of a packed crowd and millions watching worldwide. However, what Fritz didn't realize was that his headband, emblazoned with the iconic Hugo Boss logo, had been placed on upside down - a fashion gaffe that would go viral in no time.

Fritz's girlfriend Morgan Riddle - known for her immaculate style - was in the crowd watching

While Fritz's outfit for the night was undoubtedly stylish, courtesy of his sponsors at Hugo Boss, it seems he may have needed a bit more help from his team to get dressed properly. The 25-year-old player took to social media platform X (formerly known as Twitter) after the match, poking fun at himself and saying: "Yo why'd nobody tell me that s* was backwards?" The joke, however, didn't quite land well with Fritz's girlfriend Morgan Riddle, who was seated courtside cheering him on.

Riddle, known for her impeccable style and fashion sense, looked stunning in a blue jumper and matching red nails as she watched her boyfriend take on the world No 1. However, it's clear that even she couldn't help but cringe at Fritz's wardrobe blunder. As one can imagine, social media went into overdrive, with many fans taking to their accounts to share their amusement - and some, predictably, even accusing Fritz of deliberately wearing his headband upside down in a bid for attention.

The Tennis Letter blog chimed in on the drama, saying: "I guess you have to switch things up when you're 0-10 against someone." Another user joked: "Mans sobbing already," referencing the inverted BOSS logo on Fritz's headband. And then there was this gem: "If he wins tonight @HUGOBOSS needs to make hats with the logo upside down" - a tongue-in-cheek comment that poked fun at both the brand and the player.

Fritz took to social media after the match to reference his wardrobe malfunction

But let's get back to the tennis match, shall we? Fritz had been on an impressive run to the quarterfinals, taking out one seeded player en route (Tomas Machac) before facing off against Djokovic. The Serbian legend, a seven-time US Open champion and 24-time major winner, proved too strong for Fritz, winning in four sets despite some spirited play from the American.

In fact, it was an all-too-familiar story for Fritz, who has now lost to Djokovic 11 consecutive times. "It's tough," Fritz said after the match, still rubbing his headband in embarrassment. "I thought I played a good third set. But Novak's just too good."

The Italian Jannik Sinner is currently favored to lift the trophy at Flushing Meadows this year, having already made it to the quarterfinals with ease. He'll face countryman Lorenzo Musetti on Wednesday, in what promises to be an exciting matchup.

Djokovic - a 24-time major winner - proved an extremely difficult opponent for the American

As for Fritz and his wardrobe woes? Well, let's just say that this is one tennis player who won't soon forget his headband mishap anytime soon.

Riddle, known for her style, has been a constant presence throughout the tournament