The Worst-Dressed Stars At The 2025 Gotham Awards

Now in its 35th year, the Gotham Awards rarely disappoint when it comes to dragging A-listers out of their homes and onto a fancy red carpet. This year was no different, with the likes of Jennifer Lawrence, Tessa Thompson, and Elle Fanning showing up to the glitzy New York City event on Monday, December 1. With such big celebrity names, everyone was excited to see some groundbreaking and exquisite red carpet fashion — and most stars delivered. However, as with every industry event, some took it either a bit too far or not far enough and ended up becoming the worst-dressed celebs of the night.

What's most surprising about this year's Gotham Awards is the fact that some famous folks who consistently impress showed up in looks that we simply can't explain. Yes, we may or may not be talking about an ultra-famous Barbadian billionaire. But let's not get ahead of ourselves, as plenty of other stars gave Rihanna a run for her money in the worst-dressed department.

Chloë Sevigny loves taking fashion risks, and they usually pay off. Her look at the 2025 Gotham Awards? Not so much. The green minidress' bulky silhouette with long sleeves kept us from appreciating the star's beautiful hair and makeup. In fact, all we could focus on was the extra material under her armpits. Ultimately, the "Boys Don't Cry" actor's look was so ridiculous that we had to get it out of the way first. 

When Teyana Taylor walked the red carpet at the 2025 Gotham Awards, we didn't know which part of her outfit we should look at first. The "All's Fair" star wore an asymmetrical red skirt with feathers on top and a white satin tee. The actor paired the look with white shoes with black tips, creating a look that was all over the place. Unfortunately, this isn't Taylor's first fashion faux pas of the year, as she was also one of the celebs who flopped in outdated colors at the 2025 Met Gala.

Teyana Taylor's "All's Fair" co-star Naomi Watts is also no stranger to bad fashion. She was one of the worst-dressed celebs at the 2025 Golden Globes in January, and her look at December's Gotham Awards is also worth mentioning for all the wrong reasons. The actor walked the red carpet in a light-mint gown with an odd poncho-like white piece on top. Apart from the fact that the cover took away from the elegance of the gown, its white color also washed the star out.

There's always one star at an awards show who chooses to resemble a fictional character, and at the 2025 Gotham Awards, it was Zoey Deutch. The "Anniversary" actor showed up to the event in a bright-yellow dress entirely made of faux feathers, and the first thing that popped into our minds was Big Bird from "Sesame Street." Had the dress been a different color, this look could have potentially passed as fun, but with the bright-yellow shade, the resemblance is uncanny and distracting.

When it comes to Rihanna's style transformation, we truly don't have many notes. The musician's influence on fashion and trends is undeniable, which is why it pains us to include her on this list. However, her outfit for the 2025 Gotham Awards was so bad that we can't help but wonder whether the "Diamonds" singer was pranking us. From the silhouette and the shiny material to the odd headpiece, this is undeniably one of RiRi's worst fashion moments in recent years.

When it comes to Kristen Stewart's fashion, the star is all about embracing what she feels like in the moment. However, her outfit at the 2025 Gotham Awards remains a mystery to us. Vintage-looking office fashion isn't what the star usually goes for, and the garments all appeared to be too big for the star, creating a slouchy final appearance. Nevertheless, we appreciate her willingness to experiment. On a positive note, the baby bangs suit the "Love Lies Bleeding" star perfectly!

Ultra-short minidresses and dramatic push-up corsets have a place at some award shows, but Hilaria Baldwin's look at the 2025 Gotham Awards seemed out of place. Baldwin showed off her stunning figure (and rightfully so), but a dress like this one is more appropriate for a slightly more casual event — something in the realm of the MTV VMAs. Compared to all the other women who wore sophisticated gowns, this look definitely stands out (and not in a positive way).

Mary Bronstein's 2025 Gotham Awards look is proof of just how fine the line between a bad and a great fashion moment can be. The "If I Had Legs I'd Kick You" star showed up on the red carpet in a vintage-looking purple gown and donning beautiful retro hair and makeup. However, the dress' skirt was ruched in a way that created a very bulky silhouette, especially on her left side. Had the skirt been less bulky and more even, this could have easily been one of the best looks of the night.

Just like Mary Bronstein, Imogen Poots was one of the celebs whose look needed subtle adjustments to be great. Unfortunately, those weren't made, which is why the "Hedda" star is on our list. Her dress had heavy ruching in the front, a slit placed at the center of the skirt, and a matching piece of fabric that squeezed her shoulders very tightly. All of this resulted in the actor's dress looking cheap, as well as uncomfortable to wear.

"Hamnet" star Jessie Buckley showed up to the 2025 Gotham Awards in a dress that can only be described as a fashion beginner's project. While the star-studded event gave us numerous bad looks, Buckley's dress might just be the worst. The sleeves had an odd in-between length, the neckline was bland and boring, but most of all, bottom portion left us in shock. Frankly, there's not much that could have been done to save this look.