Calvin Klein’s underwear campaigns have become pop culture milestones in their own right. Over the decades, the brand has tapped music’s biggest stars – male and female – to strip down to their Calvins, sparking conversations about sex appeal, identity, and the fusion of fashion and music. From Mark “Marky Mark” Wahlberg’s infamous 1992 ads to Bad Bunny’s 2025 campaign, these moments have not only sold a lot of underwear, but also marked turning points in artists’ careers and cultural attitudes. Let us explore several eras of music icons in Calvin Klein campaigns, and how each made an impact on pop culture, body image, and the artist’s own brand.
Long before he was a Hollywood actor, Mark Wahlberg was known as Marky Mark, a brash young rapper with one huge hit – and a killer set of abs. In 1992, Calvin Klein cast the 21-year-old Wahlberg alongside a then-unknown 17-year-old model Kate Moss in a series of black-and-white underwear ads that would become legendary. Photographed by Herb Ritts, the campaign showed Wahlberg shirtless in nothing but white Calvin Klein briefs and baggy jeans, with Moss wrapped around him. The images oozed raw sex appeal and provoked a media explosion, propelling the careers of both Moss and Wahlberg and becoming one of the most iconic ad campaigns of the decade.
Those ads didn’t just sell boxers; they helped define the look of a generation. Teenage boys everywhere started sagging their jeans to reveal the Calvin Klein waistband, emulating Wahlberg’s signature style. And Wahlberg himself went from a one-hit-wonder in music to a household name. For him, strutting in his Calvins was a career breakthrough – it cemented his “bad boy” image and opened the door to acting. Even 30 years later, the sight of a buff musician in Calvin Klein briefs immediately calls back to Marky Mark’s iconic pose.
In 2015, Calvin Klein turned to music phenom Justin Bieber, who was looking to shed his teen-pop image and step into a more mature spotlight. The brand released steamy photos of a tattooed Bieber in Calvin Klein briefs alongside model Lara Stone. The black-and-white shots projected raw confidence and instantly went viral. The campaign generated massive online engagement. Bieber’s fans flooded social media with hashtags, Calvin Klein gained millions of new followers, and Bieber’s transition into adult stardom was visually and culturally cemented. The campaign wasn’t without controversy—speculations about photo editing sparked debates about authenticity and body image—but ultimately, it marked the beginning of Bieber’s new chapter. Just months later, his Purpose era would launch, and the Calvin Klein campaign became the unofficial kickoff.
By 2019, Shawn Mendes took up the Calvin Klein torch with a campaign that immediately broke the internet. At 20, Mendes posted shots of himself lounging in his Calvins, and fans responded with viral memes, breathless commentary, and a collective meltdown. It marked a turning point—Mendes was no longer the soft-spoken teen with a guitar. He was confidently stepping into his adult image, comfortable in his body and the global spotlight. The campaign wasn’t just a thirst trap; it was a milestone in how pop stars merge music, fashion, and viral relevance. Mendes’ photos trended globally and solidified him as not only a musical force but a fashion icon as well.
Troye Sivan brought a completely different energy to Calvin Klein’s legacy—one rooted in vulnerability, softness, and queer identity. First appearing in the brand’s “I Speak My Truth” campaign in 2019, and later headlining Calvin Klein’s Pride campaigns, Sivan stood out for representing a gentler, more inclusive masculinity. His appearances—whether in soft denim or rainbow briefs—resonated deeply with fans. His campaigns sparked conversations about the evolving standards of beauty, visibility for queer artists, and body representation. Sivan wasn’t just modeling; he was shifting the narrative around who gets to be sexy, strong, and celebrated. Calvin Klein’s partnership with him helped cement the brand’s progressive reinvention for Gen Z.
While male musicians often dominated Calvin Klein’s underwear campaigns, recent years have seen powerful female and non-binary artists step into the frame.
Jennie Kim of BLACKPINK has become a Calvin Klein staple. As one of the most fashion-forward idols in K-pop, Jennie’s campaigns effortlessly blend high fashion with global pop star appeal. Her 2024 shoot trended internationally, showing just how powerful the K-pop x CK crossover has become.
Pabllo Vittar, a Brazilian drag pop star, made history as the first drag queen to lead a global Calvin Klein campaign. Her Pride campaign was both fierce and historic, spotlighting LGBTQ+ visibility and cultural inclusivity on a mainstream platform.
FKA twigs stunned in a 2023 campaign that blurred the lines between art and sensuality. The striking image sparked controversy in the UK, but Twigs defended her right to express sexuality on her own terms. The ad was eventually reinstated after public support and media outcry, and it marked a key moment in the conversation about double standards in fashion advertising.
In 2025, global superstar Bad Bunny joined the ranks of Calvin Klein’s elite, starring in a campaign that mixed sensuality, swagger, and cultural pride. Shot by Mario Sorrenti and set to one of his own songs, the campaign showcased Bunny in the brand’s latest boxer-briefs and made headlines for its unapologetic Latin flair.
Bad Bunny has long challenged gender norms with his fashion, and his Calvin Klein shoot amplified that message on a global scale. From painted nails to crop tops to now leading a high-profile underwear campaign, Bunny proved that today’s masculinity is about confidence, fluidity, and authenticity. The campaign not only trended instantly—it became another major moment in his ongoing global domination.
From Marky Mark’s swagger to Troye Sivan’s vulnerability, from FKA twigs’ defiance to Bad Bunny’s redefinition of masculinity, Calvin Klein’s underwear campaigns have served as snapshots of cultural evolution. For artists, it’s a badge of honor—one that often signals a new era in their career. For fans, it’s a visual extension of the music they love. And for the brand, it’s a way to remain timeless by embracing change.
Calvin Klein has proven that underwear ads can be more than just sexy—they can be provocative, empowering, and deeply cultural. Whether it’s a viral thirst trap or a bold statement of identity, when music stars step into their Calvins, they’re stepping into the next level of their legend.
