The Worst-Dressed Stars On Valentine's Day 2025

Roses are red, violets are blue, and some celebrity outfits left us saying, "What did you do?" For us regular folk, Valentine's Day is a celebration of love, a once-a-year chance to shower the special people in our lives with affection, and that really thoughtful text. But in Celebrity Land, it's a whole different ballgame. Some stars see Valentine's as a mandatory love letter competition, holding hands just tightly enough to crush those pesky divorce rumors.

Others, however, take the chance to soft-launch their latest product, hoping we ignore the breakup whispers and that underperforming album. Whatever their motives, one thing unites them all: fashion. While a few stars swept us off our feet with their red-themed romance, others left us wondering if their stylists had finally broken up with them, over text, and in all caps.

We've accepted edgy Rihanna and made our peace with sultry Fenty Rihanna, but there's no way to justify this Valentine's date night outfit. Riri stepped out alongside A$AP Rocky in a black top, coffee-colored leggings, and an oversized camo bomber jacket — none of which seemed to be on speaking terms. We think she was aiming for high fashion, but it really just gives "laundry day, and this was all I had left." It's not just about the lack of style and color coordination; the outfit does absolutely nothing for her body. The camo bomber jacket is so bulky that even Rihanna's signature curves couldn't save her from looking like a walking rectangle. The black top was probably meant to balance things out, but once again, the jacket swallowed everything whole. Rihanna can wear almost anything, but this was not the one.

With so many shades of Valentine pink to choose from, Emma Watters, wife of Fox News host Jesse Watters, somehow picked chewable antacid pink. She paired a powdery pastel top with dark wash jeans and ruined any chance of slaying by doubling down with matching pink lipstick that sucked away all the hydration from her lips. To make it worse, she teased her hair way too high. It's not the worst outfit we've ever seen, but it's definitely stuck in an era we don't want to revisit.

Lil Nas X is known for pushing boundaries with his looks, but this outfit was a total letdown. He showed up in a thin white tank and grey sweatpants, flashing a generous amount of Calvin Klein waistband. News flash: We're a thousand Instagram posts past this trend's expiration date. Overdone underwear aside, the whole thing looked like a last-minute idea. We imagine he grabbed some roses, stepped outside, and hoped the waistband would do the heavy lifting. Spoiler: It didn't. 

It's easy to spot a campaign shoot from a mile away, and Joy Taylor's was no exception. The Fox Host's stiff pose, forced smile, and outfit seem designed more for Instagram than real life. And honestly? We're cool with that. The problem was that she looked less chic and more like a giant muppet auditioning for a lingerie ad. The fuzzy coat practically swallowed her whole, and those strategic flashes of bare skin weren't nearly enough to balance out the fuzz.

Given that Bunnie XO serves sultry looks on random days, we expected her to knock Valentine's Day out of the park. Ever the savvy businesswoman, though, she used the occasion to launch some merch of her adorable bulldog Chachi. "Chachi wants to be your Valentine," she wrote. We're suckers for animals, but Bunnie XO marketed the merch for Valentine's and didn't even feature so much as one pink heart. Instead, we got an unfortunate montage of Chachi's face that looked like it was designed in less than an hour. This look failed Valentine's, isn't good for business, and did Chachi dirty.

Timothée Chalamet's cute but awkward persona has won its way into our hearts, but there's no room in there for this outfit. Here's a tip, Tim: If you're going monochrome, skip the Pepto Bismol pink. Plus, matching your underwear to your outfit is just overkill, and not in a good way. As if that weren't enough, the wet, stringy dog hair look is doing him no favors. Instead of a heartthrob actor, he looks more like a hungover teen who fell asleep in his tracksuit. It's a no from us.

Chrissy Teigen's three different Valentine's Day outfits were all flops. The first featured a red fur coat, satin gloves, bunny ears, and a bra — need we say more? The second outfit somehow made the first look subtle — just look at the reptile, the hat devouring her head, and the feathered hips giving low-budget carnival dancer. Then came the third outfit, which could have served Victoria's Secret angel, but was ruined by the oversized hood and fluffy trim. Chrissy, we're begging, just one outfit next year.

Teal leather? On Valentine's Day? We're not saying you have to wear red or pink, but this outfit would have been better suited for a formal event. The wrinkles in the dress also cheapen the whole look and throw off the vibe completely. Unfortunately, Rory McPhee somehow manages to look even worse. The white tee, cream trousers, and that questionable belt might work for Sunday lunch with the in-laws, but not a Valentine's date. Plus, his laid-back look clashed awkwardly with Mel's sleek leather fit. Together, they looked less like a couple celebrating love and more like two old friends who bumped into each other on their way to separate events.

We see the vision, but the execution is a glaring no-no. The usually stunning Jennifer Lopez's outfit was neon pink overload that was more of a visual assault than classy or chic. Neon can be fun, but head-to-toe highlighter pink clashes hard with the softer, romantic vibe we expect from the day of love. That feathered heart piece? It looks like a piece even the costume department would reject. If Cupid had backup dancers, we're pretty sure this would be their uniform.