For those of us who have been following Katie Holmes’ career since she first appeared on TV screens as the smart, sensitive Joey Potter in Dawson’s Creek, she’s always been a fashion icon. In the late ‘90s, her wardrobe of baby tees and boyfriend jeans, corduroy jackets, floral sundresses, and overalls made her the envy of young women everywhere. And over 25 years later, her sartorial choices are still as coveted as ever. Over the past two and a half decades, Holmes’ style evolution has included timeless styles as well as calculated risks — and even a few viral moments. There are a few through lines in Holmes’ style journey throughout the years. One is her penchant for simple, effortless, and even comfortable styles. And there’s probably no better example of this than her 2019 Khaite look that caused an almost immediate sell-out of the cashmere cardigan and bra. Her love of well-made wardrobe staples is also what made her the perfect partner for A.P.C., and it’s evidenced in their recent collab that’s filled with wearable yet luxe pieces. Totally on brand for the film and TV star. That said, she’s not afraid to take a big swing every now and again. For example, who could forget her Y2K-inspired Jingle Ball outfit from 2022? The blue strapless dress over jeans may have been divisive, but it was an epic moment in her fashion history. To take a closer look at this and many more moments from Holmes’ stylish past and present, keep reading. Emmy Awards, 1998Frank Trapper/Corbis Entertainment/Getty ImagesHolmes’ little white dress from the 1998 Emmys would be totally on-trend today. Complete with a white rosette bag and romantic upswept waves, she was as angelic as her TV persona, Joey Potter. X-Men Premiere, 2000Albert L. Ortega/WireImage/Getty ImagesIn a white baby tee, low-slung snakeskin skirt, and strappy sandals, Holmes was the epitome of casually chic at the 2000 X-Men premiere. The entire ensemble could be worn today — nearly a quarter of a century later — and look just as effortlessly cool. MTV’s TRL, 2003James Devaney/WireImage/Getty ImagesHolme’s love for classically cool staples like an off-the-shoulder sweater and jeans was on display early in her career — and still continues to this day.Batman Begins Premiere, 2005J. Merritt/FilmMagic/Getty ImagesWhile attending the Los Angeles premiere of Batman Begins, Holmes showed a more elegant side in a plunging gray satin gown and sparkling strappy heels. AFI Fest, 2007Jean-Paul Aussenard/WireImage/Getty ImagesHolmes looked like a modern goddess at the 2007 AFI Fest. Her beautifully draped, asymmetrical dress was by Monique Lhuillier and she paired it with embellished thong sandals and a fresh bob haircut. Met Gala, 2008New York Daily News Archive/New York Daily News/Getty ImagesThe actor donned a Superman-inspired palette for the Met Gala’s “superhero” theme in 2008. Her vibrant dress was a vintage Giorgio Armani piece that she paired with blue pumps. Annual Style Awards, 2012Jamie McCarthy/Style/Getty Images Entertainment/Getty ImagesTo present at the Annual Style Awards in 2012, Holmes chose a black and gold Carolina Herrera gown with embellished gold heels. Met Gala, 2013Jamie McCarthy/Getty Images Entertainment/Getty ImagesIn a white Calvin Klein collection gown and Lorraine Schwartz jewels, Holmes juxtaposed her ethereal fashion with edgier hair and makeup for the event’s “Punk: Chaos to Couture” theme in 2013. New York Fashion Week, 2014Henry S. Dziekan III/WireImage/Getty ImagesHolmes started showing an edgier side back in 2014 when she appeared in a black leather look for Donna Karan’s Fall/Winter runway show at New York Fashion Week. American Ballet Theater Gala, 2018James Devaney/GC Images/Getty ImagesHolme’s oversize gray Prada pantsuit with feather trim paired with a ballet bun (appropriate for the occasion, obviously) and strappy heels was such a playful take on the traditional menswear style. Met Gala, 2019Karwai Tang/Getty Images Entertainment/Getty ImagesFor the Met Gala’s camp theme in 2019, Holmes arrived in a dramatic black and purple tulle gown with feather details by friend and designer Zac Posen. Global Citizen Press Event, 2019Gotham/GC Images/Getty ImagesHolmes’ belted navy blazer and wide leg pants were a modern interpretation of the power suit. The look was designed by Gabriela Hearst and came from the label’s Resort 2020 collection. New York City, 2019BrosNYC / BACKGRIDThe Coda star practically broke the internet when she stepped out in this Khaite cashmere cardigan and matching bra. When recently asked by Vogue magazine if she still wore the set, she replied, “No, I gave it to a friend. I was like, I’m not going to wear it again. I can’t!” Zimmermann Dinner, 2020Neil Rasmus/BFA.com/ShutterstockHolmes tried out a more retro look while attending Zimmerman’s fall 2020 show during New York Fashion Week. Her silky ‘70s-inspired set featured a graphic pattern and she finished off the ensemble with some funky frames. Vacheron Constantin Store Opening, 2021 Bennett Raglin/Getty Images Entertainment/Getty ImagesThe trendsetter always knows how to make any outfit feel more laid back and cool, even a black cutout dress. For this store opening in 2021, she dressed down the sexy style with a button down shirt and white sneakers. Tribeca Film Festival, 2022Theo Wargo/Getty Images Entertainment/Getty ImagesFor the Alone Together premiere at the 2022 Tribeca Film Festival, Holmes wowed in a white crochet dress by Chloé paired with black square-toed flats and a nude clutch. iHeartRadio Jingle Ball, 2022Dave Kotinsky/Getty Images Entertainment/Getty ImagesAnother instantly viral moment — though maybe not for the same reasons — happened when Holmes stepped onto the Jingle Ball red carpet in a Y2K-inspired look that included a TOVE strapless corset top with jeans and sneakers. Dr. Barbara Sturm Store Opening, 2022Gotham/GC Images/Getty ImagesOnce again, Holmes showed her love for NYC-based luxury label Khaite at Dr. Barbara Sturm’s store opening in 2022. This time she selected an all-leather look with wide leg pants pants and an oversized snap-button shirt. CFDA Awards, 2022Taylor Hill/FilmMagic/Getty ImagesHolmes accompanied friend and designer Jonathan Simkhai to the 2022 CFDA awards proudly wearing one of his glamorous creations, a modern take on the flapper dress. The Tonight Show, 2023NBC/NBCUniversal/Getty ImagesWith a few unique details, Holmes always makes wardrobe staples look so updated. Here, she paired her oversized Michael Kors Collection blazer with a fringe skirt for a totally unexpected combination. The Today Show, 2023Raymond Hall/GC Images/Getty ImagesHolmes’ love for cozy knitwear was once again exemplified when she appeared on The Today Show in an oversized gray sweater and splattered sequin pants to promote her directorial project Rare Objects.Red Sea International Film Festival Women’s Gala, 2023Dave Benett/Getty Images Entertainment/Getty ImagesA double breasted black Khaite skirt suit with plum colored, embellished Manolo Blahnik shoes was an equally powerful and glamorous look for the elegant event celebrating women in film. New York City, 2023Raymond Hall/GC Images/Getty ImagesHolmes chose another Jonathan Simkhai look while out and about in NYC in 2023. Her relaxed fit suit felt so spring-y in this butter yellow shade. Chanel Dinner, 2024Gilbert Carrasquillo/GC Images/Getty ImagesFor a Chanel dinner in 2024, Holmes donned another cardigan and bra combo. This time she gave it a more nighttime feel with a vampy lip and diamond jewelry. American Ballet Theater Spring Gala, 2024James Devaney/GC Images/Getty ImagesThe avid American Ballet Theater supporter picked a Pucci Spring 2024 kaftan-style gown to attend the Spring Gala in 2024. (Stay Up To Date)Become A Style InsiderJoin The Zoe Report’s exclusive email list for the latest trends, shopping guides, celebrity style, and more.