The Worst-Dressed Celebs Of Valentine's Day 2026 Made Us Lose Faith In Love

Each year, Valentine's Day brings us plenty of fun celebrity looks. Whether they are spotted out and about for a fun night or photographed at a red-carpet event, the rich and famous tend to up their fashion game on February 14. However, not everyone's looks end up giving us the good kind of stomach butterflies. Last year, we talked about the worst-dressed celebs on Valentine's Day 2025, and let's just say that 2026 had its own fair share of distressed fashion and exposed skin.

While the expectations for celebrity Valentine's Day fashion aren't necessarily red, pink, and feminine, we do expect good tailoring and wrinkle-free fashion moments. However, stars like Dua Lipa, Charli XCX, and Cindy Crawford have shown us that even the rich and famous who have limitless access to the best stylists can make fashion mistakes. And none of these looks are absolutely dreadful, but they could have been executed better or simply worn to a different occasion. On Valentine's Day, we anticipate looks that inspire love, but these disappointing 'fits left us heart-broken instead. 

Dua Lipa had a fancy Valentine's Day red-carpet date with her boyfriend Callum Turner at the 2026 Berlinale International Film Festival, attending the premiere of his film "Rosebush Pruning." The "Levitating" singer wore a piece by Chanel which was as see-through as a beach cover-up. Had she worn it over a black bodysuit, it would have been much more glamorous; instead, her cheekiness stole the spotlight from her partner and his project. However, this isn't the musician's first foray into bad fashion choices — we've already talked about Dua Lipa's seemingly inappropriate wedding guest dress.

'90s supermodel Cindy Crawford attended the Keep Memory Alive "Power of Love" gala on Valentine's Day 2026 in Las Vegas, Nevada. The beauty walked the event's red carpet alongside her husband Rande Gerber, and while the two looked great as always, Crawford's dress was kind of an eyesore. In particular, the cutouts on the black number changed shape because the dress' material was too soft, drawing all our attention away from the model's natural allure.

Hollywood star Naomi Watts was spotted on Valentine's Day 2026 in New York City, and her outfit was definitely showing more than we expected. Even though the star was technically covered from head to toe in fabric, her dress featured sheer paneling across her chest. We assume that the paneling was meant to be a bit higher, but it ended up moving down as Watts walked, freeing the nipple on a cold New York City night and revealing that Watts was braless. The risky moment aside, the dress was also incredibly wrinkly, which is something that can instantly ruin a look.

Hilaria Baldwin is no stranger to a style faux pas — she was one of the worst-dressed stars at the 2025 Gotham Awards. Less than three months later, Baldwin once again entered bad-fashion territory, this time on Valentine's Day. The wife of actor Alec Baldwin attended the ALICE + OLIVIA presentation in New York City in a floral maxi skirt and a top that made her cleavage the focal point. Unfortunately, the grandma-couch pattern of the bottom and sexy cut of the top clashed, creating a completely incohesive look.

While the stunning style transformation of Charli XCX showcases just how versatile the pop star's look is, her 2026 Valentine's Day outfit left plenty to be desired. The "Guess" singer showed up at a press conference for her film "The Moment" in Berlin, Germany, in a black dress that was completely distressed, with fringe-like pieces falling below the hemline. Now, while this is clearly a gothic-inspired look that is supposed to be bold and shocking, it doesn't really scream Valentine's Day and thus seems out of place.

As a redhead, Natasha Lyonne looks stunning in aqua blue, which is why it's a shame that her outfit ended up on our list. However, when the "Orange Is the New Black" star was photographed heading to the LaQuan Smith fashion show in New York City, it was clear that her dress was a couple of inches too long, dragging along the pavement. Tailoring is crucial for a perfect fashion moment, and a dress that is too long can quickly go from fab to drab.

Valentine's Day 2026 was a working day for Pamela Anderson, who attended events for her film "Rosebush Pruning" in Berlin, Germany. The actor showed up to a photocall in a poncho-like minidress that created an incredibly odd silhouette. Later that day, Anderson walked the red carpet at the Berlinale International Film Festival in a dress by Carolina Herrera, wearing a giant scarf/sheet that made her look as if she had just rolled out of bed. While the stunning style transformation of Pamela Anderson is proof that she's constantly changing her look, her Valentine's Day fashion needs an upgrade.