7 Times Katie Holmes' Outfits Should Have Landed Her On The Worst-Dressed List

It's hard to believe that Katie Holmes could ever walk out of her apartment in a bad outfit. But even fashion icons make mistakes now and again, and Holmes is no exception. The star normally hits it out of the park when it comes to style, and continues to get better and better. Nothing shows this more than Holmes' style transformation from "Dawson's Creek" to NYC. She went from playing sweet, innocent Joey Potter to strutting her stuff like the queen of Manhattan. In fact, she's so frequently dubbed a fashion icon that Holmes has actually spoken out about how she feels being called a style icon, and what makes up her fashion philosophy. Best of all, Holmes has undergone a complete transformation following her divorce from Tom Cruise, and she's evolved into a more sophisticated, daring version of herself after getting out of that relationship. 

It's precisely this level of daring and play with fashion that we love about Holmes. She uses clothing creatively, bending fashion norms and surprising us continuously. Within this space of experimentation, Holmes has stepped out in a few flops, but they're worth it considering how many wins she's had. And the rest of us can feel much better about our failed outfit experiments, since Holmes has done it too. 

At the Tony Awards in 2025, Katie Holmes wore an emerald green blouse with a floor-length pink skirt, both by Prada. While one would think that the combination of Holmes and Prada would be fool-proof, the outfit was a big miss. The top looked boxy and the skirt slumped down to the floor as if it hadn't been fitted properly for Holmes' body. The two pieces did not work well together and didn't do Holmes justice. 

Katie Holmes attended the Ulla Johnson show during New York Fashion Week on February 11, 2024 wearing a skirt and top by the designer. She wore an Ulla Johnson white lace-trimmed silk, sleeveless top and coordinating midi skirt, pairing the pieces with black boots. While Holmes herself looked magnificent — her hair and makeup were perfection — the lace getup looked frumpy on the normally-stylish star. The diagonal hem of the skirt and the lack of any silhouette made the outfit look ill-fitting on her. 

For the opening night of the Broadway production of "Our Town" at the Barrymore Theatre in New York City in October 2024. Holmes went for a black outfit, wearing a black blouse by Heirlome and a black maxi skirt by the same brand. While Holmes looked radiant, the black was too sombre on her, and she drowned in the ample fabric from the blouse, with its long wrists, and full skirt. Holmes always looks so good in bright colors that her red carpet outfit from that night left us wanting something more.

Nothing beats Katie Holmes walking around New York City in jeans. It (almost always) leads to absolute perfection. However, on one particular day in December 2024, Holmes stepped out in oversized blue jeans, a black coat with a gold belt, and a black beanie hat with a small side braid. Both the jeans and jacket were boxy and slightly oversized, and the small braid and hat lacked the voluminous proportions that long, full hair would have provided to the overall look. To be fair though, New York City is cold in December, and Holmes probably just wanted to stay warm and keep things chill. 

Katie Holmes attended the premiere of "The Kennedys: After Camelot" in March 2017, where she joined the late Matthew Perry, a co-star on the show. Holmes played Jackie Kennedy Onassis while Perry played Ted Kennedy. For the occasion, Holmes wore an ankle-length, blush gown in velvet with lace panels. The whole outfit was a flop. The dress lacked that wow-factor we've come to expect from Holmes. The silver clutch seemed out of place with the warm, rose gold tones of the outfit, and her hair looked messy. It was a moment where the red carpet fit did nothing for Holmes. 

Katie Holmes is the absolute goddess of casual, cool-girl street style, but when it comes to red carpet events, she tends to bring out the dazzle. Unfortunately, this was not the case at the Gold Meets Golden Benefit on February 21, 2015. Holmes arrived in black jeans, a denim shirt by Saint Laurent, a black neck scarf, and a beige Celine belt bag. For a day of errands, it's a lovely, relaxed look, but for a benefit, the outfit is entirely too casual and uninteresting. It looks like Holmes rolled up after doing the school pickup. 

Katie Holmes attended the "Miss Meadows" premiere at the Tribeca Film Festival on April 21, 2014 in New York City. For the event, she wore a burgundy off-the-shoulder dress with geometric shapes at the waist. The jutting waist wasn't the best look on Holmes, and the rest of the dress was uninteresting. While Holmes can usually kill it when it comes to hair and makeup, even if the outfit is bad, her hair at this event was also unfortunate. Her hair looked choppy and unstyled, hiding her beautiful face.