How BOSS turned Taylor Fritz’s headband mishap into a marketing win
At the Dallas Open this week, the headband accident has become an asset.
When Taylor Fritz walked on court to play Novak Djokovic in the quarterfinals of the US Open last September wearing his trademark Boss headband upside down so it read “SSOB,” I thought it might be intentional. Fritz—whose dry sense of humor has become more apparent in recent years with social media hits like “You almost had him”—seemed like the kind of person who might do that. Or perhaps it was some kind of new superstition, a symbolic way to reverse his fortunes against Djokovic? With professional athletes, you never know.
But after the match he made it clear it was a true mistake, writing on X, “Yo why’d nobody tell me that shit was backwards.” Of course, the fact that not only he didn’t catch it but no one else on his team did made the whole thing even funnier.
A few Boss executives happened to be in the stands that night but didn’t notice the error from afar until their phones started blowing up with texts and photos, according to a Boss source who was not authorized to speak publicly. There was a moment of panic until they looked up at Fritz’s friends and family in the stands and noticed them all wearing the headbands upside down in support. “It was so serendipitous and I was like we’ve got to leverage this—it’s so iconic and reflective of who he is,” they said.
Texts to Fritz’s agent at IMG and the social team in Germany (who were asleep) ensued, and the next morning the brand had a post up on Instagram showcasing the upside down headband with copy that read, “When things turn on their head, literally, Bosses get back up. Now onto the next Taylor! #SSOB.” The image of the headband on their e-commerce site was also turned upside down for a short period. It added unusual levity to a disappointing loss and showed that Boss—a premium German brand that’s typically more reserved—could have some fun.
“We were able to do that because Taylor is so fun and carefree,” said the Boss source, noting that because Fritz himself wanted to lean into it felt authentic rather than forced.
This is where so many athlete-brand moments fall apart: when the joke belongs more to the marketing team than to the athlete himself.
But for both the brand and Fritz, it’s become more than just a funny blip in time. At the Dallas Open this week, where Boss has been the apparel sponsor since 2025, the company has built an entire universe around this happy accident, turning a one-night mistake into a repeatable visual system.
Like last year, the ball kids are decked out in Boss, but this time they’re all wearing the headbands too—like a bunch of Fritz clones running around the court.
A Boss pop-up store located near the practice courts which sells the latest Boss collections alongside its Dallas Open Capsule is marked by a Boss headband floating from the ceiling like a crown. Tongue-in-cheek instruction cards are present throughout the shop, guiding shoppers on how to properly put on the headband.
For Fritz’s first match tonight against fellow American Marcos Giron, Boss is also hosting an in-stadium sweepstakes. They’ll be handing out complimentary Boss headbands as people file into their seats and will randomly select two guests who are wearing the headband for seat upgrades during the match. It’s the rare kind of logo saturation that doesn’t read as forced, because it’s rooted in a story most fans will understand.
“I started wearing the headband because it felt natural to me, but it’s grown into something fans really recognize as part of my identity,” Fritz said via email. “Working with Boss to celebrate that is special because they’re all about confidence and style, which is exactly how I want to feel when I step on court.”
As for whether or not the headband moment or Fritz himself have impacted sales, the Boss source said that the brand is starting to over-index in their active and sportswear category. While they work with other athletes like the Dallas Cowboys, they attribute a lot of the growth to their tennis athletes (the brand also works with Italian player Matteo Berrettini) and involvement in tournaments like Dallas and Stuttgart.
Tennis has quietly become one of the few sports where brands can test lifestyle expansion in real time—on court, in retail, and across social—without the noise of a massive league ecosystem.
While Boss has no current plans to sign new tennis players, the brand is bullish on the racquet sports space at large, recently gifting product to the New York Hustlers pickleball team. And they always have their eye on new tournament opportunities, which have been a boon to sales and brand awareness. “Racquet sports are just a really fun space for us to play in that aligns well with our brand,” said the Boss source.
In an era where brands spend months trying to manufacture authenticity, Boss benefited from something rarer: a very human mistake and a marketing team smart enough not to overthink it.
Thanks for reading! If you have tennis news or tips to share, email jessica@hard-court.com. For regular updates, follow Hard Court on Instagram.
Everything about this headband blunder, the marketing spin off and, especially, this story is just so fun. I smiled throughout. Thank you. It’s great to see how fully Boss has embraced him and his style. This is the dynamic all brand sponsor partnerships should emulate.
Love this. I'm so not a fashion person but I love tennis, and these pieces always give me such a fun new insight into the sport