The Worst-Dressed Celebs On Valentine's Day 2025

Regardless of whether you're in a relationship or not, Valentine's Day offers a wonderful excuse to dress up and go for a look that you wouldn't necessarily wear otherwise. And while the rich and famous dress up all the time, we expect them to also look their chicest and most holiday-appropriate on Valentine's Day, too.

This year, many stars delivered. For instance, Kylie Jenner, who supported her boyfriend Timotheé Chalamet at the Berlin International Film Festival on February 14, was chef's kiss in a stunning bedazzled black number. However, while some nailed Valentine's Day fashion, a few celebs disappointed us. Some could have saved their looks with minor tweaks, while others wore pieces we really didn't need to see. Then again, fashion is very personal, and while we weren't big fans of some sartorial choices, we do accept the fact that the folks who wore these outfits might have loved them. Having said that, here are, in our opinion, the worst-dressed celebrities from Valentine's Day 2025, from Rihanna to Lady Gaga.

While Oprah Winfrey doesn't do much wrong, the talk show host isn't immune to a wrinkly outfit. On Valentine's Day 2025, Winfrey attended the 40th Santa Barbara International Film Festival, and when she walked out on stage to present the Montecito Award, we couldn't help but think about how much her look would benefit from some steaming. Now, we get it — she was sitting in her light-gray pantsuit, which can lead to wrinkling, but her stylists should have known better than to dress her in a pantsuit made from an easily wrinkled material. After all, everyone knew she would be photographed, and sadly, the pictures didn't look great.

"Believe" singer Cher was photographed while arriving at the "Saturday Night Live 50th Anniversary Special" on Friday, and while we know that she was going to change inside, we were still hoping the star would serve us some more fashionable Valentine's Day clothing outside. While heading to the event, the star wore a pair of sweatpants, a zip-up hoodie, and a puffy, black-and-white jacket. Add her pink-an-purple makeup and very-shiny hair to the mix, and the look was all over the place.

We're so happy that Lady Gaga is back to her early 2010s pop era with the viral song "Abracadabra," and we wouldn't want Lady Gaga to stop taking big fashion risks. However, Gaga's Valentine's Day outfit served us everything but lovey-dovey fashion. The musician was photographed in New York City in a dramatic black piece that featured mesh, ruching, and a waistband for a look that evoked a Morticia Addams vibe. We love that's in theme with her upcoming album, "Mayhem," but it's more Halloween than Valentine's Day — and it's the same reason she was one of the worst-dressed celebs at the 2025 Super Bowl last week. Ultimately, Gaga isn't one of the celebrities who have nailed method dressing this Valentine's Day.

"Wednesday" star Jenna Ortega attended the "SNL50: The Homecoming Concert" this Valentine's Day, and unfortunately, her look wasn't one of our favorites. While the golden disco top was pure perfection, the two brown suede pieces threw us off. The shades simply didn't match, yet they weren't different enough for it to seem like it was done on purpose, which is why we wish the star had ditched the coat. Jenna Ortega is known for her striking style, so this fashion faux pas definitely came as a surprise.

Pop star Rihanna was spotted leaving a courthouse in Los Angeles, California, on Valentine's Day, and while her look wasn't horrible, we expected a bit more from the Savage X Fenty founder. Yes, she was going to court, but hey, we all deserve a little RiRi-meets-Elle-Woods magic. The "Smurfs" actor wore a green maxi dress that gave grandma vibes, and even though Rihanna paired it with snakeskin boots and edgy orange sunglasses, the look still wasn't as fun or sultry as we'd expect from her. That said, Rihanna has undergone a stunning style transformation over the years, so we're hopeful her next Valentine's Day look will pop a bit more.

When "Bridesmaids" actor Kristen Wiig walked the "SNL50: The Homecoming Concert" red carpet on Valentine's Day, we couldn't help but think of all the fashion mistakes she was making. First, the event called for a fancier top than a bright-yellow sweater with cutouts down the sleeves, especially considering the role that "Saturday Night Live" played in her career. Sill, while we can forgive the sweater, we absolutely can't forgive the black stockings. Marla Maples' outdated outfit at the 2025 Grammys made the same mistake, and Wiig repeated it just two weeks later.

Musician Alessia Cara of "Scars to Your Beautiful" fame visited SiriusXM's studios on February 14, 2025, and for the occasion, she decided to wear a cozy maxi sweater dress. Unfortunately, the grays of it washed the star out, making it look like she wasn't feeling her best. If you ask us, Cara was missing a pop of color that could've been added with something as simple as a statement bag.

Hungry for more? Check out the most lavish celebrity Valentine's Day gestures.