Taylor Fritz’s headband sponsor may have been left a little disappointed on Tuesday night after the American tennis star accidentally put it on upside down for his big US Open quarterfinal against Novak Djokovic.
The No 4 seed headlined Arthur Ashe in one of the biggest nights of his career so far, simultaneously giving Hugo Boss some important air-time for their brand.
But when putting on his outfit in the locker room before the match in New York, Fritz inadvertently placed his headband on upside down, making it difficult to read when shown on screen.
Things went from bad to worse for the California native when he was later dumped out of the US Open in four sets.
Despite putting up a late fight, winning the third set, he was dominated by his Serbian opponent, losing an 11th straight match-up against him.
Hilariously, the American’s first comments after coming off court were about the headband, when he took to X to write: ‘Yo why’d nobody tell me that s*** was backwards.’
Fritz’s wardrobe blunder, meanwhile, is made more notable by the pristine style of his girlfriend Morgan Riddle, whose outfits are always styled perfectly… and perhaps he’ll wish she was present before the match to correct his error.
Taylor Fritz inadvertently put his headband on upside down before heading out on court

Fritz’s girlfriend Morgan Riddle – known for her immaculate style – was in the crowd watching


Fritz took to social media after the match to reference his wardrobe malfunction
She was inside Arthur Ashe for the big game, regularly shown on TV in a blue jumper alongside her boyfriend’s coaching team.
Riddle also had red nails for the occasion and could be seen pumping her fist in her man’s direction whenever he won a big point in the match.
Some on social media claimed Fritz’s upside down headband was a deliberate decision, meanwhile, with popular blog ‘The Tennis Letter’ writing: ‘I guess you have to switch things up when you’re 0-10 against someone.’
Another joked ‘Mans ssobing already’, referencing the SSOB ordering of the letters on his backwards BOSS headband.
A third made the point that Hugo Boss should make the most of the marketing opportunity, writing: ‘If he wins tonight @HUGOBOSS needs to make hats with the logo upside down.’
But it was a difficult first set for the American, who quickly fell behind in spite of his superior seeding to the legendary Novak Djokovic, seventh favorite heading into the tournament despite his record 24 major titles.

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

Riddle, known for her style, has been a constant presence throughout the tournament
Fritz has enjoyed a quietly impressive run to the quarterfinals at Flushing Meadows, staying under the radar and only needing to beat one seeded player en route to the last eight.
That victory came in the previous round against Tomas Machac, and Tuesday’s showdown with Djokovic marked the first time Fritz was slated for a match on the main Arthur Ashe court at the US Open.
Fritz got to the final at Flushing Meadows in 2024, eventually losing in straight sets to world No 1 Jannik Sinner.
The Italian is once again favorite to lift the trophy, and he’ll face his countryman, 10th seed Lorenzo Musetti, in the quarterfinals on Wednesday.