Kendall Jenner isn’t just delivering punchlines in her new Super Bowl 2026 commercial, but she’s also serving serious fashion inspiration.
The supermodel stars in Fanatics Sportsbook’s “Bet on Kendall” campaign, where she pokes fun at the long-running “Kardashian curse” rumor surrounding her dating history with professional athletes. But alongside the humor, Jenner showcases two standout looks that capture both her laid-back and jet-set style.
In one scene, Jenner lounges around a sprawling mansion and sunbathes poolside wearing a black high-cut one-piece swimsuit. The minimalist silhouette features thin straps and a dramatically high leg, highlighting her long lines and signature model-off-duty aesthetic.
With barely-there styling and natural makeup, the look leans effortlessly sexy and relaxed, which is the kind of timeless swimwear moment Jenner is known for.
The swimsuit scenes are intercut with shots of Jenner wandering through the lavish estate, reinforcing the commercial’s tongue-in-cheek premise that her luxurious lifestyle is fueled by her so-called “cursed” dating history rather than her wildly successful modeling career.
Later, Jenner switches gears with a more polished, vintage-inspired ensemble as she heads toward a private jet. She appears in a sleek white cutout dress that hugs her figure, styled with a silky headscarf tied under her chin, dark sunglasses, and strappy heels.
The look channels classic Riviera glamour with a modern edge, equal parts Old Hollywood and contemporary cool.
Completing the jet-set fantasy, Jenner carries structured luggage and poses beside a vintage black car, adding to the cinematic feel of the moment. The outfit stands in sharp contrast to the relaxed swimwear, showing her range from poolside minimalism to refined elegance.
Jenner is not naming names in the ad, but fans hardly need a roadmap. Over the years, she has been linked to a number of NBA players, including Jordan Clarkson, Blake Griffin, Ben Simmons and Devin Booker. Clarkson and Jenner dated briefly in 2016, followed by a relationship with Griffin from 2017 to 2018. She was later on and off with Simmons for about a year beginning in 2018.
Her most high-profile and longest-running athlete relationship was with Phoenix Suns guard Devin Booker. The two dated on and off from early 2020 until October 2022 and were even spotted together again at dinner in Miami in September 2024, fueling brief reconciliation rumors.