The Worst-Dressed Stars In Critics Choice Awards History

The Critics Choice Awards red carpet has had its fair share of noteworthy fashion moments. Some are iconic for all the right reasons — who could forget Zendaya's pink Tom Ford breastplate or Natasha Lyonne's plunging Saint Laurent gown? — whereas others are cautionary tales. From bold statements gone wrong to confusing missteps that could easily have been avoided, fashion fails have rocked the Critics Choice Awards year after year.

The red carpet has seen everything, from tuxes that seemed like last-minute efforts to elaborate dresses that might've been inspired by birdcages or bedsheets. Even some typically fashionable A-listers you would never associate with poor sartorial choices — think Natalie Portman or Timothée Chalamet — strike out from time to time, proving that not even the best in the game can escape fashion criticism unscathed. Here are some of the worst-dressed stars in Critics Choice Awards history. 

Judy Greer has made a number of sartorial missteps at the Critics Choice Awards. Digging into every last one of her questionable red carpet moments could fill pages, but for now, we would like to bring attention to just two of the "13 Going on 30" star's fashion fails. The first one is from 2019, when Greer turned up at the award show in a dramatic Reem Acra gown. Thanks to the bulky and almost stiff look of the floral-patterned material, it resembled vintage upholstery. 

2023 was no better, when she switched gears to a colorblocked design that had none of her earlier dress' extravagant prints. Even so, the black Greta Constantine gown failed to hit the mark, consumed by a billowing yellow overlay that fell asymmetrically down the silhouette. What's maddening is that Greer's fashion choices always seem to have potential, but what ultimately shows up to the red carpet falls just short.

Before the advent of instant online takedowns, Nicole Kidman slipped a questionable red carpet look past the masses at the 2003 Critics Choice Awards. She was nominated for "The Hours" that year — a momentous occasion that should have called for something more red carpet chic than what she wore. Her top and skirt combo was very boudoir, like something plucked from either the lingerie or nightgown section of a store, even though it was a Chanel look fresh off the runway. 

The coordinated ensemble seemed like a half-baked attempt at dressing up, with the net detailing and overdone patterns doing Kidman zero favors. The only thing that popped about her look were her curls. It's not that the whole appearance was bad; it was just underwhelming for someone who was up for one of the bigger awards of the evening. Oh, the 2000s. A very different time, indeed.

Kiernan Shipka's outfit at the 2018 Critics Choice Awards left a number of critics likening her to a mermaid, some of whom even praised the bold combination of materials, colors, and textures. We definitely get the mermaid comparison, but we don't necessarily see it as a good thing. Sure, we appreciate the use of dreamy pastels, the attempt at a creative silhouette, and Shipka's understated and chic hair and makeup, but there are a lot of things we do not like about this red carpet ensemble. As far as we're concerned, this did not make the right kind of splash.

The sea foam green skirt, the scale-like patterns on the pants and the top, the long fluorescent yellow bow that looked like a tail, the big bows on the shoulders — we could go on and on. Don't get us wrong, we love a little glitter-and-frills action, but this brand of whimsy might have better suited the Met Gala red carpet. 

Ariana Grande's 2025 Critics Choice Awards look was many things, but sadly, it was not elegant. Her Dior Couture dress featured a cage that rested along her waistline, with floral appliqués and fringes trailing loosely down to her feet. It was clearly designed to draw attention. And it did, just not in the best way. Grande's confusing outfit landed her among the worst-dressed stars at the 2025 Critics Choice Awards, from where no amount of Glinda's witchy powers could have rescued her. 

Interestingly, as fantastical as her ensemble was, it wasn't one of the charming vintage dresses Grande sported all through "Wicked" season at red carpets. According to Vogue, Grande's golden birdcage painstakingly took an approximate of 4,000 hours to make — a feat that deserves its own shoutout — but the result unfortunately ended up looking more costume than couture. Oh well, it was a prison of its own making. 

In 2011, Khloé Kardashian brought some of that good ol' Kardashian glam to the Critics Choice red carpet with a look that was inevitably bold and completely uninterested in playing by the rules. It was a short strapless dress that featured a long train and animal print all over. Now, animal print is nothing Hollywood award shows haven't seen before, but the kitschy Y2K aesthetic it gave off made Khloé look more club-ready than red carpet-ready. 

"Leopard print has been my thing forever ... it's timeless, chic, and always in style," Khloé once told Elle. And in light of her T-shirt-worthy quote "When in doubt, leopard," this fashion choice hardly seems surprising. The only mark it hit for us was the interesting contrast it created with her sister Kim Kardashian, who opted for a plain burnt sienna Vera Wang gown, when the pair went up on stage to present together. 

The decades roll on, but Ione Skye's look at the 2004 Critics Choice Awards remains an unforgettable masterclass in last-minute styling to this day. The "Say Anything" star showed up to the award show in an ensemble that looked like it had been dug out from the bottom of a laundry basket, with no time to consider if it was even presentable. The lack of accessories and what looked like zero hairstyling pretty much drove that point home, too. 

Her long white skirt, which featured a striped design and asymmetrical netting, seemed like a complete mismatch with her coat-style top that looked like it was a few sizes too small. Everything from the awkward neckline to the sleeves bunched up near her wrists screamed untidy — and it felt like Skye was all too aware of this, given the presumably uncomfortable poses she hit while taking pictures on the red carpet. 

Comedian, actor, writer, and director Bo Burnham has taken some big creative swings throughout his career, and many of those swings have yielded tremendous results. Alas, the bold sartorial risk the "Eighth Grade" filmmaker took at the 2019 Critics Choice Awards fell flat. He showed up to the award show in a monochromatic Thom Browne suit that looked like it was going through an identity crisis, with the coat divided down the middle in a black and white contrast. 

While GQ did note that the event was momentous for the risky suits men dared to flaunt in exchange for boring black tuxes — and we're all for this subversion — they made a pertinent observation about Burnham's strange outfit: "Two-toned suiting is generally best left to Batman villains. Generally." The look landed the comedian on some worst-dressed lists from that year's Critics Choice Awards.

Maggie Gyllenhaal's acting career is impressive, but when it comes to her fashion game on the Critics Choice red carpet, the record hasn't been so great. In 2003, she arrived in a drab brown dress that could have well been fished out of any millennial's wardrobe from that era. The very Y2K outfit featured an almost daring neckline tied together with a drawstring, embellished sleeves, and an asymmetrical hem that dragged awkwardly past her knees. 

By 2005, she tried to dial up the drama — a bit too much, it appeared. She showed up to the award show in a bright red ensemble that was too overwhelming for its own good with floral patterns, neckline ruffles, and bow detailing. It looked like something a doll might wear. Today, both styles can be filed under the zany aesthetic that defined 2000s fashion, which may have essentially been bold but not always beautiful. 

Greta Gerwig's red carpet record is punctuated with fashion fails, several of which have taken place at the Critics Choice Awards. Gerwig turned up to the 2016 event in a striking red and black gown that had too much of everything — neckline ruffles, accordion pleats, drab aesthetics. Gerwig looked like an art project of her own making, with her stiff stance doing little to salvage the turnout. 

The pattern repeated itself in 2024, this time with an outfit that contrasted 2016's frills and fancies. Gerwig's plain white Molly Goddard gown exuded melodrama — and not the good kind. It had a big billowing skirt that looked like rumpled bedsheets, while the fit of the top was awkwardly boxy. It more or less looked like Gerwig cut some armholes into a pillowcase and called it a blouse. It was bedroom-core at its finest, and no, we don't mean that as a compliment.

Katie Holmes' style transformation over the years has been fascinating to watch. And while she has (almost) always been the epitome of elegant dressing, there is one misstep we wish we could forget from her lookbook: her 2008 Critics Choice outfit. The "Dawson's Creek" star turned up to the award show in a one-shouldered champagne Lanvin dress that seemed like an odd mix between classic Grecian and towel drape aesthetic. 

The glittery number, with its soft pleats and stylish asymmetrical cut, had great potential but hung a little too limply off Holmes' frame, giving off a vibe that was more shapeless than effortless. The bland color palette didn't do much to flatter Holmes' overall appearance either, especially given the lack of accessories. While we're not fans of the toga, we would be remiss not to take a moment here and give Holmes' uber-chic, sleek hairdo a well-deserved shoutout for carrying the whole look. 

Boots Riley got out of bed and walked straight onto the Critics Choice red carpet — or so it seemed. The "Sorry to Bother You" director showed up to the 2019 event in a belted, striped silk bathrobe over what appeared to be a suit and button-down shirt. The rich and luxe purple palette of the robe was quite stunning, but the overall ensemble still felt a little too sleepy for an award show. The oversized fit swallowed his frame whole and with it, any redeeming factor the color could have offered.

In a sea of high glamor, Riley's ensemble hit far below the mark. We couldn't help but think of the terry cloth bathrobe and towel combo Rita Ora sported on the 2017 MTV EMAs red carpet before she changed into about a dozen more outfits while hosting the show. While Ora's bathrobe was clearly a tongue-in-cheek joke about not having enough time to get ready, Riley's bathrobe was more of a snooze.

One need only take a look at Kristen Bell's appearance at the 2009 Critics Choice Awards to get a complete idea of what Y2K "glam" was all about. The then-star of "Veronica Mars" had on a silver tube dress, paired with chunky neck jewelry and a very "Jersey Shore" hair pouf.

The dress' flimsy fabric was a rumpled, crumpled mess when she was on the red carpet, and we can't imagine it looked much better as the night went on. As GoFugYourself quipped, "This dress was not made for sitting. It also... maybe barely was made at all." Oh, and don't get us started on the way the dress drooped down in the front but also hiked up in the back. And the backless detailing? Well, that didn't help the case at all. It's a look best forgotten in the 2000s, from whence it came. 

"Squid Game" star HoYeon Jung turned up to the 2022 Critics Choice Awards in a dress that presented a challenge she would not win. The Louis Vuitton creation featured, first and foremost, a vintage bustle that jutted out from her waist and was layered with an asymmetrical skirt that landed limply at her ankles. The heavily embroidered, loose-fitting bodice did her no favors either. The look invited comparison to everything from lampshades to clothes hangers on social media.

Frankly, we couldn't make sense of what exactly was going on here either, and Jung's explanation to Vogue was of little help. "My look for last night was a nod to Old Hollywood glamour, but with a modern edge," she said, adding that it was "inspired by the passage of time." The only inspiration it should have evoked was for Jung to leave the bustle back in the 19th century, where it belonged. 

At the 2006 Critics Choice Awards, Ludacris rolled up in an oversized black blazer and baggy red trousers. Of course, oversized and relaxed silhouettes, when done well, can be super stylish, modern, and becoming. Alas, this particular combo was a whole lot of wrong. 

When styling baggy clothes for a flattering fit, there's a fine line between chic and overwhelming. Unfortunately for Ludacris, his '06 Critics Choice Awards outfit fell in the latter category. The blazer hung off his frame far too casually while his trousers pooled at the top of his shoes. You could've told us that he borrowed this from someone two sizes larger than him at the last minute and we might've believed you. What's more, Ludacris was wearing what looked like a vest and a patterned button-down shirt under his blazer, and the layers only created more awkward bulkiness. While we're all for comfort in fashion, it never hurts to make it a tad elegant. 

Joey King's transformation as an actor has been stunning. Her fashion choices at the Critics Choice Awards in recent years, not so much. In 2020, for example, she wore a metallic silver floor-length dress that tied at the shoulders. While it might sound cool and edgy on paper, under the lights of the Critics Choice red carpet, the Prada gown ended up looking like a big wad of wrinkly aluminum foil that someone attempted to smooth out. 

Five years after that, King went for a daring Miu Miu dress that featured ruffles, lacework, sheer details, and a drab color palette that might have been fashionable a few centuries ago. Alas, in 2025, all this ensemble delivered was a vintage lingerie aesthetic that served neither viewers nor King herself. As if we needed another reason to not like the look, the garment had a strange slit up the back that did zilch to elevate the already unflattering cut of the skirt. 

Matthew McConaughey accepted his best actor trophy for "Dallas Buyers Club" at the 2014 Critics Choice Awards in an outfit that was far less impressive than the performance that earned him the honor. His gray patterned coat and bowtie combination, though classic, somehow managed to give an off-the-rack vibe. Maybe it was the too-snug tailoring or the contrasted lapels, but the fashion gods were just not on McConaughey's side that day. 

Despite the sheen of the fabric — or maybe because of it — the attire lacked polish, making him look more like a magician or a ringleader than an award-winning A-list actor. If McConaughey had a top hat to complete his look, we would have half expected him to pull a rabbit or two out of it. Hey, at least that would have been more exciting than the dull ensemble he settled on that evening. 

Throughout 2016, Natalie Portman served up some of the best maternity red carpet looks of all time, going from award show to award show with her baby bump on full display. Each of the actor's ensembles was better than the last... until her fashionable streak ended at the Critics Choice Awards, that is. The "Black Swan" star showed up in a cape dress by Alexander McQueen that was rather busy. The garment featured asymmetrical cuts, red frills, floral prints, a high neck, and more. 

Basically, there was a lot going on and very little of it was good. The too-edgy aesthetic landed far away from Portman's other, more elegant red carpet appearances through awards season, thanks in large part to the cape that hung off her shoulders and consumed her whole frame. It was pure design chaos and Portman would have fared much better even in a plain, simple gown. The only saving grace about the dress, in our opinion, was its loose fit that probably kept a pregnant Portman super comfy through the show. 

In recent years, Timothée Chalamet has experienced quite the transformation — especially when it comes to his personal style. The Oscar-nominated actor has made a lot of truly major moves when it comes to fashion, often shaking up menswear norms. While we are more or less fans of Chalamet's willingness to step outside of the box, his color-splashed suit at the 2019 Critics Choice Awards was a little too hammy and costume-y. A bold number from Alexander McQueen, it definitely stood out among the other attendees' traditional black tuxes, but it did not exactly leave a positive impression. 

British Vogue would quickly dub this look Chalamet's "Most Zany Suit Yet," and of course, this would not be the last time he'd wear a suit that would get tongues wagging. But as far as the actor's style history is concerned, we wish we could forget this particular suit. The white chunky sneakers further added a confusing touch of streetwear to this life-sized paint palette aesthetic Chalamet was trying to pull off. It might have been a fun fashion moment but when every look tries to break the mold, even quirkiness can end up getting boring after a while.