Katie Holmes Has Been a Denim Style Icon for 20 Years

In life and fashion, I only know two things for certain: Katie Holmes loves denim and denim loves Katie Holmes. From the back of Tom Cruise’s motorcycle to the cover of Glamour, the actor, director, and mother of one is living proof that jeans can be styled for any occasion or context. She’s worn them to sit courtside at Knicks games and front row at New York Fashion Week. She’s worn them to dine at fancy restaurants and walk countless red carpets. Recently she made headlines for reviving a controversial Y2K denim trend at the 2022 Jingle Ball.

The state of denim dressing is always in flux. Inseams and waistlines rise and fall. Silhouettes expand and contract. Trends come and go. But Holmes has managed to stay ahead of the curve for decades now. She had the foresight to ditch her skinny jeans for wide-leg and baggy styles a full calendar year before Gen Z declared them “over” on TikTok. And unlike the rest of us circa 2013, she never stopped wearing jeans and ballet flats—a move that must feel gratifying now that the aesthetics of the 2010s are coming back with a vengeance.

“I’m not really a fashion person,” Holmes admitted to Harper’s Bazaar in June. Everyone wants to “look nice” for premieres, she hedged, but jeans and a vintage tee (preferably a bit dirty or stained) is her truest form. Like a rom-com lead come to life, Holmes looks stylishly undone—comfortably haphazard even—but unmistakably herself. After all, when style muses like Aaliyah, Selena Quintanilla, Carolyn Bessette-Kennedy, and Jane Birkin wore jeans, they were doing more than setting a trend. They were making a certain kind of relaxed, off-duty-model glamour feel instantly attainable for the rest of us simply by reaching into our own closets.

Looking to cultivate a little of Katie’s unfussy, all-American elegance in your own wardrobe? Start here with a 20-year tour of her ever-growing denim collection.

The pair she wore at the height of Dawson's Creek

The year was 2001, and Katie Holmes—a classic beauty cast for her sad, furtive eyes—was in her Joey Potter era. Sporting a longline leather blazer, a black crewneck sweater, and what appears to be a pair of Asics, this self-styled ’fit for a stroll with her mother is a nod to ’90s minimalism amid the fashion excesses of the early 2000s.

<h1 class="title">Actress Katie Holmes With Her Mother in NYC</h1><cite class="credit">Arnaldo Magnani</cite>

Actress Katie Holmes With Her Mother in NYC

Arnaldo Magnani

The bootcut jeans she wore to the 2002 MTV Movie Awards

Apparently, everyone—Charlize Theron, Reese Witherspoon, and Natalie Portman included—wore bootcut jeans to the MTV Movie Awards in 2002. On hand to present an award, Holmes was the ultimate girl next door in a gauzy black tank, faded jeans, and pointed-toe boots with a stiletto heel.

<h1 class="title">2002 MTV Movie Awards Katie Holmes</h1><cite class="credit">Gregg DeGuire</cite>

2002 MTV Movie Awards Katie Holmes

Gregg DeGuire

The whiskered, low-rise Sevens she wore to Sundance

Premium denim wasn’t really a thing until 7 For All Mankind hit the market like a meteor in 2000. Owning a pair of Sevens instantly became a status symbol and an essential part of the early-aughts It girl uniform. Celebrities like Britney Spears and Beyoncé were avid fans of the brand then, and the likes of Selena Gomez and Vanessa Hudgens still are now.

In a look so trendy that it accidentally became timeless, Holmes accessorized a low-rise whiskered pair of Sevens with Uggs and a bucket hat at the 2003 Sundance Film Festival.

<h1 class="title">2003 Park City - The 7 for All Mankind Lodge</h1><cite class="credit">James Devaney</cite>

2003 Park City - The 7 for All Mankind Lodge

James Devaney

The pair that marked a vibe shift in 2004

In 2004 we begin to see a more feminine, refined version of Katie Holmes emerge. Pictured here in a crisp white blazer accented by cherry red peep-toe pumps and a matching Louis Vuitton clutch, Holmes was still on the arm of then fiancé Chris Klein. But two weeks later her life would change forever after a fateful interview with Seventeen. “I used to think that I was going to marry Tom Cruise,” she admitted on the sunny rooftop bar of the Gansevoort Hotel, unwittingly setting in motion a string of events that culminated in her engagement to the action star the following summer.

<h1 class="title">Celebrity Screening of "Fahrenheit 9/11" - June 29, 2004</h1><cite class="credit">Fred Duval</cite>

Celebrity Screening of "Fahrenheit 9/11" - June 29, 2004

Fred Duval

The pair she wore on the back of her new man’s motorcycle in 2005

Welcome to the dawn of TomKat. At the height of their whirlwind romance, Holmes and Cruise were both in the thick of blockbuster press tours—Batman Begins for her and War of the Worlds for him. At first their all-consuming devotion to one another felt like a publicity stunt. A month after their first public appearance as a couple, Cruise jumped on Oprah’s couch to declare his love for Holmes. And less than a month after that, Cruise proposed to Holmes at the Eiffel Tower. Clad in jeans, black jackets, and sporty sunglasses, the freshly engaged pair waved to the press before boarding a train to Marseille.

<h1 class="title">Tom Cruise Heads To Marseille For "War Of The Worlds" French Premiere</h1><cite class="credit">Francois Durand/Getty Images</cite>

Tom Cruise Heads To Marseille For "War Of The Worlds" French Premiere

Francois Durand/Getty Images

A week later Holmes arrived at a Los Angeles fan screening of War of the Worlds beaming on the back of Cruise’s motorcycle—very Mrs. Mission Impossible, if you ask me. “Do you ever wonder whether this is just a honeymoon phase?” W magazine reporter Robert Haskell asked her around this time. “Tom and I will always be in our honeymoon phase,” Holmes, then 26, replied earnestly. By the end of the year, the happy couple announced they were expecting a child.

<h1 class="title">"War of the Worlds" Los Angeles Fan Screening - Arrivals</h1><cite class="credit">Kevin Winter/Getty Images</cite>

"War of the Worlds" Los Angeles Fan Screening - Arrivals

Kevin Winter/Getty Images

The slouchy Prps pair she borrowed stole from her husband in 2008

After marrying Cruise in a celebrity-studded Italian castle wedding and giving birth to their daughter in 2006, Holmes marked the beginning of her hot-working-mom era with two iconic haircuts. First a chin-length bob with blunt bangs in 2007. Then a tousled Victoria Beckham-esque pixie cut in 2008.

Katie kicked off the year with a starring role in Mad Money, then spent spring and summer preparing for her Broadway debut in the revival of Arthur Miller’s All My Sons. She was often photographed walking to rehearsals in oversized sunglasses and boyfriend jeans, carrying binders, travel mugs, and multiple designer bags. Holmes was caught wearing a certain pair of cuffed Prps jeans so often that her stylist Jeanne Yang was asked to share their backstory. The jeans, Yang revealed, actually belonged to Cruise. A few weeks later the lovebirds doubled down on the look by wearing matching Prps denim for a night out in New York City.

NEW YORK - AUGUST 06:  Katie Holmes is seen on the streets of Manhattan on August 6, 2008 in New York City, New York.  (Photo by James Devaney/WireImage)

Celebrity Sightings in New York - August 6, 2008

NEW YORK - AUGUST 06: Katie Holmes is seen on the streets of Manhattan on August 6, 2008 in New York City, New York. (Photo by James Devaney/WireImage)
James Devaney

The denim minidress that reflected her state of mind during the divorce year(s)

As we’d later learn, month(s) of planning went into a “brilliant” multiphase divorce strategy concocted by Holmes and her attorney father. Steps included quietly renting an apartment, using burner phones, and distancing herself from mutual friends while conspicuously keeping up appearances. Holmes and Cruise arrived hand in hand at the 2012 Vanity Fair Oscars party in March. Holmes even flew to Reykjavik, Iceland, with Suri to visit Cruise on the set of Oblivion two weeks before filing in late June.

Divorce papers obtained by TMZ, however, told a different story. The marriage, Holmes said, had been “irretrievably” broken for at least six months. Perhaps that’s why Holmes looked remarkably put together amid the collapse of her marriage. Within days of going public about the proceedings, three generations of Holmes women were spotted enjoying a sunny day out at Chelsea Piers.

“I’m fascinated by what she’s been wearing,” The Cut’s Charlotte Cowles told The New York Times. “It’s simple, relatable clothing. She’s playing the mom role she wants to portray herself as: a loving parent and as a normal person, America’s sweetheart. It’s a clichéd term, but Tom Cruise is a wild card, and she knows she needs to play the opposite. She’s been very smart.”

NEW YORK, NY - JULY 10:  Kathleen Holmes, Katie Holmes and Suri Cruise arrive to Chelsea Piers on July 10, 2012 in New York City.  (Photo by James Devaney/WireImage)

Katie Holmes And Suri Cruise Sighting In New York City - July 10, 2012

NEW YORK, NY - JULY 10: Kathleen Holmes, Katie Holmes and Suri Cruise arrive to Chelsea Piers on July 10, 2012 in New York City. (Photo by James Devaney/WireImage)
James Devaney

The denim skirt she wore to pick up Suri from school in 2013

Imagine looking this good to pick your daughter up from school. To me, the slightly wrinkled crewneck sweater confirms that Katie pulled this fall ’fit from her closet, not a styling rack. The hat and oversized shades are doing double duty as paparazzi deterrents, but this doesn’t look or feel like a disguise. Her dark-wash denim skirt falls just above the knee, directing the focus to those deliciously slouchy burgundy leather boots. The gray hat and sweater provide balance by keeping the rest of the look neutral.

<h1 class="title">Celebrity Sightings in New York - September 26, 2013</h1><cite class="credit">NCP/Star Max</cite>

Celebrity Sightings in New York - September 26, 2013

NCP/Star Max

The Calvin Klein Jeans shirt and Stella McCartney jeans she wore on the cover of Glamour

In her cover interview for the August 2014 issue, Holmes talked about the place denim holds in her heart and wardrobe. “I do like to buy my own clothes because I like to support designers,” she told friend and designer Zac Posen over cheese fries. “I know the work that goes into it. I have a tightly edited closet. I like what I like. And I repeat a lot. But I’m always comfortable in jeans—I feel like I can really do anything when I’m in them.”

The denim jumpsuit she wore with a blazer to the US Open in 2017

“I liked the combination of denim with the tweed, but it was a little bit more modern because it was a jumpsuit,” Holmes said of the Ralph Lauren RRL jumpsuit and blazer in an interview with Elle UK. “It was a little bit tomboy mixed with preppy. Anytime you put denim in, I’m like, ’Yesss.’”

<h1 class="title">Celebrity Sightings in New York City - September 7, 2017</h1><cite class="credit">Gotham</cite>

Celebrity Sightings in New York City - September 7, 2017


The skinnies she wore with the most coveted cashmere bra on the internet

A newly single Holmes broke the internet in 2019 when she hailed a cab in this oat-colored cashmere bra and cardigan from Khaite, which sold out immediately after she was photographed wearing it. Wearing the cardigan almost falling off the shoulder with a single button clasped, Holmes paired the knit set with skinny jeans and black leather mules from Acne Studios.

Of the viral outfit, Holmes told Elle UK, “I thought that the idea of like a cashmere sweater with a cashmere bra underneath just sounded really cozy and had a little hint of sexiness but just not trying so hard. And I thought, Oh, that’s kind of cool; I don’t know where I’ll ever wear it, but I think I’m gonna give it a try. Because it also, to me, was like, oh, that would be something that you would wear in a photo shoot because it looks like you could style it right, but it would, might be hard in real life. I don’t know. I’m not really a show-a-lot-of-skin type of person. I mean, I’m happy for the cardigan.” Of the Phillip Lim bag, which is facing the wrong way, she said, “I was like, living my daily life and I didn’t really know if it was this way or that way.”

<h1 class="title">Katie Holmes' cashmere bra and matching sweater has become the fall's must have fashion item!</h1><cite class="credit">BrosNYC/Backgrid</cite>

Katie Holmes' cashmere bra and matching sweater has become the fall's must have fashion item!


The Reformation wide-leg jeans she couldn’t stop wearing

Holmes created this elegant daytime ensemble with her former stylist Allison Bornstein (who subsequently went on to create the three-word method, a TikTok-viral formula for developing your personal style).

On top, a white pussy-bow blouse is layered with a textured brown blazer and billowing beige trench coat. Luxe accessories like her Chanel flap bag and Prada sunglasses are made to feel more lived-in with the addition of a high-rise, wide-leg crop from Reformation—proof that Holmes was an early adopter of the 2021 anti-skinny jean trend.

<h1 class="title">Celebrity Sightings In New York City - February 10, 2020</h1><cite class="credit">Gotham</cite>

Celebrity Sightings In New York City - February 10, 2020


The controversial dress-over-jeans she rocked at the 2022 Jingle Ball

Holmes took a lot of heat for this Y2K-inspired look featuring a Tove strapless bustier minidress worn over Reformation Wilder jeans with a nose ring and a pair of New Balance sneakers. On Twitter, some called it cursed. Others said she ate. Many found it hard to believe the photo was taken in 2022, not 2002. Days later, stylist Brie Welch defended the look in The New York Times.

“We decided the rich color and subtle bustier effect detailing of the top was elegant and would be fun if paired with jeans, creating a more youthful feel for Jingle Ball and the atmosphere there,” Welch wrote via email, adding: “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.”

In other words, let Katie Holmes live! We’re all going to be eating our words when Bella Hadid copies this look later.

<h1 class="title">iHeartRadio Z100's Jingle Ball 2022 – Press Room</h1><cite class="credit">Dave Kotinsky/Getty Images</cite>

iHeartRadio Z100's Jingle Ball 2022 – Press Room

Dave Kotinsky/Getty Images

Originally Appeared on Glamour