Katie Holmes Red Carpet Outfits That Were Total Disasters

There's no denying that we are utterly obsessed with Katie Holmes. Whether we're wondering what led to Jamie Foxx and Holmes' split, ruminating over her ill-fated marriage to Tom Cruise, or simply feeling nostalgic about "Dawson's Creek," the fangirling never ends. Of course, as well as being an actor and a pop culture icon, Holmes has largely established herself as a style queen. Some of her best looks over the years have shown us how casual can be super chic, and when she nails it on the red carpet glam, everyone else may as well go home. However, like many of Hollywood's most recognizable stars, Holmes isn't immune to getting it wrong at times, either. 

Even the most well-versed fashionistas have been known to step a Louboutin out of line on the way to greatness, haven't they? It's practically a rite of passage. From her early days in the spotlight and trying to figure out what to wear to which event, to more recent appearances at major award shows, Holmes has found herself on more than a couple of worst-dressed lists. Does it make us worship her any less? Absolutely not, but it's time to take notes and learn from her mistakes so we don't have to commit them ourselves — should we ever actually be invited to a red carpet event, that is.

The Tony Awards is always a fabulous occasion that brings out the theater world's most fabulous stars. In 2025, Katie Holmes arrived on the red carpet wearing an interesting ensemble that divided opinion among fashion pundits across the globe. The green and pink color combo was a risk in itself, but the ill-fitting high-neck green blouse paired with the pink embellished maxi skirt really pushed this outfit into dangerous style territory. Some thought it was a nod to the iconic green and pink color palette of the hit musical "Wicked," but something tells us this isn't a look that Glinda would be proud to rock to the Ozdust ballroom. 

The outfit was a custom Prada creation. It might have been intended as a fun and playful take on red carpet fashion, but the cut and texture of the blouse worked against the delicacy of the embellishment of the skirt to create an aesthetic that felt unfinished, unpolished — and simply put, not award-worthy. Both items could've been worn separately for something that may have resembled a decent outfit, but in this case, it's a massive thumbs down from us. Who would've known that Prada could look this rumpled? 

Ah, young celebrity love in the aughts, was there anything quite like it? We can't forget the biggest romances of the era, from Ryan Gosling and Rachel McAdams to Ben Affleck and Jennifer Lopez. Before Holmes met and married her childhood crush, Tom Cruise, she was in a serious relationship with "American Pie" star Chris Klein. The pair dated for five years before calling it quits, but during that time, they attended countless events together, including the 2003 Louis Vuitton Gala. Klein wore a sleek (if not slightly too large) black suit for the night out, while Holmes wore a white floral dress embellished with ruffles. Though the dress itself wasn't particularly offensive, it didn't suit her style at all, or her coloring. 

Holmes has olive skin and suits an autumn palette, so dressing in white made her look washed out. The dress stood out against her skin in a way that appeared harsh and unforgiving, and it wasn't helped by the low ponytail and two slivers of bangs, nor the golden box purse she carried, which clashed terribly. We love a cute, ditsy floral moment, and while this outfit would've likely looked great on someone with Kirsten Dunst's hair color and skin tone, it didn't tick a single box for Holmes. The lack of jewelry also puts added emphasis on the dress, and if we could hop in a time machine and give Holmes one piece of advice, it would be to ditch the chunky watch in favor of something dainty that would complement the outfit. Shoulda, woulda, coulda.

We've been following Katie Holmes' drastic style transformation over the years, and while there have been some fantastic highs (hello girl-next-door chic), there have been some truly questionable lows. In 2008, Holmes attended the "All My Sons" Broadway opening afterparty wearing a strange and yet oddly fascinating jumpsuit. Now, we loved a jumpsuit moment in the 2000s just as much as everyone else, but it had to be done right. The ensemble featured a black lace neckline with long sleeves before billowing out into a loose-fitting, silken white torso and pants. The balloon-leg stopped at Holmes' ankle to display black pumps with thick straps and a stiletto heel. 

We know that white isn't Holmes' color. It drains here and takes the warmth from her gorgeous natural tone, but that's not the only problem with this outfit. It seems to be trying to blend a modern style with a vintage touch, drawing on inspiration from the flapper era while also trying to establish dominance as a noughties trend. We love a star that takes risks with their style, but this is one choice that didn't pay off. There was simply too much going on. On the plus side, we adored Holmes' short haircut as it framed her delicate features perfectly — it just wasn't enough to distract us from the outfit hiccup. 

We know there are fashion trends from the '00s that deserve to make a comeback. We're here for chunky belts and scarf tops. After all, what goes around comes back around, and we are nothing if not slaves to style nostalgia — but it has to be done right, doesn't it? Looking at this photo, you might be forgiven for thinking this was taken in the '90s or early '00s, before Katie Holmes became a style icon we could all look up to. Amazingly, dear reader, that's not the case. Holmes rocked this outfit when she attended the 2022 Jingle Ball, and to say it was controversial would be an understatement. Holmes wore a formal blue dress/top from Tove, over a pair of baggy jeans from Wilder. She finished off the look with a pair of sneakers, much to our confusion. 

Millennials weren't a fan of seeing the dreaded jeans and dress trend make its way back to the forefront of fashion, and the criticism didn't go unnoticed by Holmes' stylist, Brie Welch, who told The New York Times it was supposed to be fun, young, and playful. However, the sneakers were Holmes' touch. "On the day of (and because Katie has her own effortless style that should be appreciated here), she said she wanted to wear sneakers, because it was a concert and obviously there would be a lot of dancing to Dua Lipa," explained Welch. Just because something feels justified doesn't mean it always works.

In 2008, the stunning transformation of Katie Holmes was fully underway. The actress had been married to Hollywood heartthrob Tom Cruise for two years by this point, and their high-profile romance was at its peak. That's not to say that the star always stepped out with her beau, though. Holmes attended the Critics' Choice Awards solo that year and wore a sparkling Lanvin dress for the occasion. While her make-up and hair were arguably on-point, the gown hung awkwardly below the knee and draped across her svelte frame from her right shoulder, drowning her in fabric. 

From certain angles, Holmes' right arm was fully camouflaged, giving her a tilted appearance, while the beige color washed the "Dawson's Creek" alum out, despite her deep tan. Holmes doubled down on the flesh-colored style fatality by finishing off the look with nude peep-toe pumps. We can't help but feel that color is your friend in situations like this, and so is knowing what cuts suit you and what cuts don't. Instead of highlighting her petite frame in the best possible way, the gown turned homes into a block-shaped catastrophe. Not to mention, the length was simply awkward.

While Katie Holmes won't make our Met Gala: The most outrageous outfits of all time list with her bold yellow 2014 ensemble, it's a close call. Compared to some of the looks we saw in the years that followed, Holmes' Marchesa dress isn't over-the-top, or gaudy, or even particularly bad — but at the time, she topped worst-dressed lists across the internet. Media outlets and style commentators took issue with everything from the hue of the dress to the crinkled fabric and red beading along the corset. Holmes also came under fire for her unkempt brunette locks, but was this simply a gown that was too fashion-forward for its time? 

The following year, Rihanna wore her instantly iconic bright yellow Guo Pei dress to the Met Gala and was praised for it, so it's possible that among Holmes' style missteps was bad timing. There's no denying that the star nailed the theme of the evening, which was Charles James: Beyond Fashion, but even that didn't win her any points.  

While it might've not resonated with critics, the person who wore the gown was happy as Belle in a sprawling library. "I feel amazing!" she told Us Weekly. "I love the color, and I love the romance of it, and I love the embroidery. They do such beautiful embroidery, and I feel of a different time in it." 

There's nothing we love more than good tailoring. A well-fitted pair of pants with a blazer can be a timeless and classic outfit that we never get sick of, but what about when tailoring goes awry? There's rarely anything worse. In 2018, Katie Holmes attended the premiere of "The Wife" wearing a monochrome look that felt more suited to a parent-teacher conference than a red carpet. We don't love Holmes in white as it clashes against her beautiful autumn coloring and olive skin, but the issues don't end there. The floppy, stark white blazer created an awful base for the entire look, but it's the black high-waisted pants that we really can't understand. Holmes has a slender frame, but the masculine cut of the pants swamped her around her mid-section. 

The loose fit mixed with the structural failure of the blazer had us scratching our heads in wonder. Even though it appears to be a more casual premiere than we're used to, it's not an excuse to throw out the stylebook and go totally rogue. We're also not a fan of the turquoise pendant that added another element of confusion into the mix — but, on the flip side, we're never angry at a sleek black pointed pump. 

There's no denying that Katie Holmes was never the same after her divorce from Tom Cruise, but back at the height of their romance, we were sure it was the real thing. The A-list couple was the talk of the town in the noughties, and they didn't keep their marriage out of the limelight. In August 2008, Holmes accompanied Cruise to the premiere of "Tropic Thunder," and she didn't go for a natural look. The star rocked a pixie cut and opted to go for a distinctly vampy vibe that didn't quite work out. The leather, tiered halter top was paired with a long black skirt, but it's really the makeup that makes this one of Holmes' worst red carpet looks. 

With dark, smoky eyes and a deep red lip, we can't help but feel that Holmes, then 29 years old, looked like she was trying to look more mature. While everyone ages naturally and the actor can't stay the eternally fresh-faced Joey Potter we remember from the '90s, there's something to be said for having a lighter hand in the glam department. Holmes may have been aiming for a sultry, femme fatale aesthetic here, but the elements didn't quite gel together enough for it to be well executed. 

There have been some truly painful red carpet looks that left us wincing over the years, and this might just be one of the biggest offenders. Although it could be argued that it was a different time, we simply can't take that as a valid excuse for Katie Holmes' "Matrix: Reloaded" premiere look in 2003. Homes attended the event with her then beau, Chris Klein, but it didn't look as though they were about to walk the carpet at an A-list event. Instead, Holmes' polka dot blouse, jeans, and black pointed flats combo gave us just-rolled-out-of-bed, and not in a chic Parisian way. There are a million ways that jeans can be elevated to make an outfit a little less slouchy and plain, but Holmes hadn't yet learned the ropes. 

This look may have been acceptable for a night out at the movies in your hometown as a teenager, but as one of the decade's biggest stars? We have to pass. We can't say that Klein scored much better here, with a brown blazer over a white t-shirt, jeans, and sneakers. The '00s vibes were present and accounted for in all the wrong ways.

We can't help but feel that movie premiere styling has never quite been Katie Holmes' forte. In 2004, she appeared at the premiere for the disaster movie, "The Day After Tomorrow," wearing a dizzying green and yellow dress that floated down to her calves. The spaghetti straps seemed to be working overtime, and while Holmes certainly had (and still has) the type of frame that can pull a look like this off, the gown itself was far too busy to do her any favors. The silhouette was kind of meh, and pairing the outfit with pumps in a different shade of green just added another layer of unwelcome complexity to the ensemble. 

Holmes' choice of accessories seemed a little bizarre here as well. The bright yellow shoulder bag was chunky and bulky, making the relatively dainty dress appear ill-thought-out and poorly chosen. We all love a decent purse that can keep all of our essentials in, but this feels like an outfit better suited to running errands at the grocery store than for rubbing shoulders with Tinseltown's elite. On the plus side, we're not mad at the star's subtle makeup and simple up-do, which accentuated her dainty features perfectly. We're nothing if not fair.