Last year, when Katie Holmes attended the iHeartRadio Z100’s Jingle Ball, she almost broke the internet. Soon after her red carpet appearance, the internet was buzzing over her risk-taking look: a navy mini dress paired with light-washed mom jeans. And while the combination was, for many, a definite no-no, Holmes made us all rethink. After all, she looked as beautiful and confident as ever.
To us, that’s the beauty of Holmes’ style, ever-evolving and yet always stylish and elegant. Whether it’s a red carpet look or something she wears to run errands, the actress always looks incredible.
“I enjoy [fashion],” the Dawson’s Creek alum once told Glamour. “I mean, I enjoy the craftsmanship. I enjoy putting things together. And I work with [stylist] Brie Welch, and she’s very detail-oriented, and that inspires me. I think it is very creative.”
To check out some of Holmes’ best looks over the years, dating back to 1998, scroll below!
So Angelic (1998)
Back in 1998, Holmes turned heads at the 50th Annual Emmy Awards in this beaded white gown with a matching floral purse.
Not Afraid of Color (2000)
At the 2000 MTV Awards, Holmes brought some color to the carpet in this multicolored green, orange and pink dress. The origin of a fashionista!
Sticking to Classics (2002)
At the 2002 MTV Movie Awards, Holmes opted for staples anyone has in their closets: blue denim pants and a black shirt. Simple yet timeless!
Perfect in Print (2003)
In 2003, Holmes dared to experiment on the carpet, including this red and gray floral printed look for the premiere of Pieces of April.
Finding Her Style (2003)
Speaking of experimenting, Holmes opted for this more mature black, white and green look in 2003. If you ask us, the outfit felt a little too dated for her at the time.
Keeping It Comfortable (2003)
In many carpets through the years, including this one for VH1, Holmes has proved that being comfortable and relaxed is her priority.
Sexy Back (2004)
Holmes also knows how to bring sexy to the carpet, like in this ultra-low back moment at the 2004 Vanity Fair Oscar Party.
Down for Denim (2005)
Throughout the years, there’s one thing Holmes has made crystal clear: her love for denim. On red carpets and beyond!
Figure-Flattering (2005)
While Holmes doesn’t always show much skin for the carpet, she has a talent of choosing dress and outfits that perfectly complement her slim figure.
Red Takeover (2005)
At the German premiere of Batman Begins, Holmes perfectly matched the carpet in this strapless red dress.
Belle of the Ball (2005)
At Oprah Winfrey’s Legends Ball in 2005, Holmes perfectly complemented her soon-to-be-husband Tom Cruise in this layered white dress.
Baby Bump Onboard (2006)
While pregnant with her daughter, Suri, Holmes didn’t attend many red carpets. A month after giving birth, however, she attended this Mission: Impossible III premiere beside Cruise. For the event, Holmes opted for a classic LBD.
Suit Up (2006)
Despite it being less common, Holmes experimented with more masculine and less figure-hugging styles, like this wide-legged suit, in the 2000s.
Inner Goddess (2007)
Holmes embraced her dark side at the AFI FEST in 2007 in this one-shoulder draped gown.
Shades of Nude (2007)
While Holmes’ street style might get her the most praise, the actress’ red carpet repertoire is to die for.
Runway Ready (2007)
Holmes looked breathtaking at Armani’s Spring/Summer 2007-2008 Haute Couture show in this ivory strapless dress with a beaded bodice.
Embracing the Short Hair (2008)
In 2008, Holmes went through a major hair transformation and chopped it off in a chic bob. To show off her new look, Holmes wore this nude-colored one-shoulder dress to the 13th Annual Critics’ Choice Awards.
A Leg Moment (2008)
Speaking of embracing her brand new ‘do, Holmes also showed off her legs in this bright red jacket while attending the Late Show with David Letterman.
A Classic Color Palette (2009)
Much like many of us, Holmes often rocks an all-black look that is both easy to style and a chic style moment.
Wear the Carpet Meets the Street (2010)
At 2010’s Sundance Film Festival, Holmes broke some fashion rules by wearing this seemingly street-style look to the red carpet. We’re totally here for a risk taker!
All in the Styling (2016)
While these wide-legged pants and this cropped sweater aren’t that unique on their own, Holmes’ decision to style them together with dark pink lips pulled it all together.
Met Ready (2016)
At 2016’s Met Gala, Holmes leaned into her dark, grungy style in this embroidered navy dress with ultra-long hair.
Classic for a Reason (2016)
While a black suit is a classic, Holmes’ choice is going shirtless under it at the 2016 Tribeca Film Festival made it totally unique.
Boho Chic (2017)
While attending a Cartier cocktail party in 2017, Holmes showed just how good the bohemian aesthetic looks on her in this beaded nude-colored dress.
Staying Simple (2018)
In one of our favorite gowns of hers, Holmes wowed at the Brooks Brothers Bicentennial Celebration in 2018 in this figure-hugging wine-colored dress.
Slight Variations (2019)
While Holmes has worn suits many times to the carpet, this gray looks with feathered hems made it super unique.
Leading Lady (2019)
Speaking of suit, the actress looked breathtaking in this royal blue suit and nude heels back in 2019.
Head-Turning (2019)
Holmes steered clear of her more casual style and absolutely turned heads at the 2019 Met gala in this purple and sheer black halter dress that was equally dramatic and elegant.
All About Cutouts (2021)
To prevent the look from being a little too sexy for her taste, Holmes accessorized with a matching black cardigan at the Vacheron Constantin Flagship Grand Opening.
Rule Breaker (2022)
At the red carpet for the iHeartRadio Z100’s Jingle Ball in 2022, Holmes wore the now-infamous navy mini dress and mom jeans. But, despite breaking a few fashion rules, she still looked incredible.
Too Cool (2023)
And while her red carpet style is always incredible, Holmes’ eye for street style, like in these paint-splattered pants and cozy sweater, has us pinning to our favorite Pinterest boards every time we see them.
Bringing Her Street Style to the Carpet (2023)
Holmes has also honed in on her ability to transform her street style edge into stylish red carpet looks.
Elevating Denim (2023)
Once again, Holmes proved she can turned her street style up a notch at this year’s CHANEL Tribeca Festival Women’s Lunch.
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