7 Outfits That Put Katie Holmes on the Worst-Dressed List

Katie Holmes ordinarily dressed soft and sweet in the noughties, but took a weird turn on the 2000 MTV Movie Awards red carpet. She selected a skin-tight colorful velvet dress with a plunging V-neck and a thin choker. The worst part was the noticeable seam down the middle of the dress which caused the design to be off center and unaligned. But the mismatched colors are what landed Holmes on Marie Claire’s “Worst Ever MTV Movie Awards Fashion” list. The outlet even called the color explosion “disturbing.” 

When Katie Holmes made her Broadway debut in 2008, she wore classic black and white to the opening-night premiere. But the colors were in the form of a huge, misshapen white jumpsuit that was covered with black lace on the neck and sleeves. Glamour named it one of the year’s worst, calling the jumpsuit “strange.” This was not a great year for Holmes when it came to style, as she topped Telegraph’s worst-dressed list in 2008 as well. 

The 2014 Met Gala theme celebrated Charles James, who was known for his structural designs with grand draping. Katie Holmes wore a huge canary-yellow strapless dress with cranberry-colored accents on the bodice that looked more like blood stains. The big yellow dress landed her on the worst-dressed list by E! News, which said simply, “There’s so much dress!” Unfortunately, the crinkling of the dress material just appeared messy. Holmes was definitely drowning in fabric, but she could have gone for a bold makeup look by pairing yellow blush (which is more wearable than you’d think) with this dress.

The Huffington Post included Katie Holmes on one of its earliest “Week’s Worst Dressed” lists of 2015 for her boring attempt at monochrome. At Berlin Fashion Week, Holmes wore a gray overcoat atop a neutral turtleneck sweater. She dressed up the outfit with knee-high boots and a giant gray hat, but it wasn’t enough to make the outfit look at all lively. The outlet pointed to “the muted colors washing her out” which definitely kept Holmes from standing out in this ensemble.  

There are definitely elements of Katie Holmes’ 2018 Grammy dress that could’ve worked. But the unforgiving dark color and highly-textured pattern ended up on Taste of Country’s worst-dressed list for the Grammys that year. The description that Taste of Country gave the look included phrases like “reminiscent of Emily Dickens” and “a hint of ‘trash bag'” — ouch. It definitely didn’t help that the red-carpet backdrop was the same shade of jet black and made Holmes drift out of focus. The lining was shapely on her body, but looked heavy on her small figure as if it were weighing down the actor.  

It seems as though Katie Holmes was trying to channel the Y2K “dress over jeans” trend at the iHeartRadio Jingle Ball in 2022. She wore a strapless navy-blue top with the slightest side cutouts and bootcut jeans with black sneakers. The ensemble was giving vibes of wearing Forever 21 at a middle school dance and was named as one of the night’s worst by Life & Style, given that the “strapless top didn’t complement” the denim. With tired jeans and the most basic black sneakers, there was no saving Holmes from this fashion flop.

Katie Holmes received rave reviews for her return to Broadway in the 2024 revival of “Our Town.” But her return to the Tony Awards red carpet was not nearly as triumphant. Holmes wore a bizarre two-piece ‘fit that included a green top with oversized sleeves tucked into a floor-length pink skirt with crystal detailing. Her top looked more like a trash bag than tasteful dress material. Naturally, it made Glam’s list for the worst-dressed celebs at the 2025 Tony Awards.