Katie Holmes has been a denim style icon for 20 years and here’s proof

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 US, 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. 

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.