Katie Holmes Has Always Been The Ultimate Y2K Muse

If you could time travel back to your teenage years, would you rewear anything from your closet? Maybe a pair of flared jeans or a micro-mini skirt. But probably only a few styles, right? Katie Holmes, on the other hand, could pull off anything from her teens with ease. Once the A-lister burst on the scene with Dawson’s Creek in 1998, she immediately became one to watch on the fashion front. From the late ‘90s through the 2000s, Holmes was the face of numerous Y2K trends, including sheer pieces, ballet flats, and slip dresses (to name a few). And to no surprise, these fads are just as prevalent in her aesthetic today as they were 25 years ago.

One of her most iconic numbers? Slip dresses. Some celebrities need at least a few red carpet events to establish their personal style. But not Holmes. At the 1997 New York Film Festival, Holmes made her red carpet debut in what would become classic Holmes attire: a lacy black slip dress. Two years later, she attended the Eyes Wide Shut premiere in a lavender slip dress underneath a cool-girl cardigan. Fast forward to the 2010s and you’ll see her slip streak has only strengthened.

If you’re a longtime Holmes fan, you know in the early 2000s, she was also hardly spotted without ballet flats on. Since then, ballerinas, Mary Janes, and every flat in between have maintained their status in Holmes’ wardrobe. Starting in 2008, she was especially fond of flower-embellished flats from Alaïa. On the street style scene, she frequently alternated between the French brand’s version and a metallic Lanvin pair alongside low-waisted jeans, elongated blouses, and slouchy Chloé bags.

Holmes has since retired her Alaïa and Lanvin options, however, this made room in her closet for more modern silhouettes. For instance, she can’t get enough of Lemaire’s square-toe leather flats. Most recently, on Sept. 6 Holmes coupled them with a feminine white blouse, gray straight-leg jeans, and her go-to carry-all from Khaite.

In recent years, Holmes has even styled Y2K combos that she missed in real time. While she never publicly tapped into the dress-over-pants trend in the 2000s, Holmes made up for it at the iHeartRadio Jingle Ball in Dec. 2022. Inside Madison Square Garden, she walked the red carpet in a navy blue mini dress overtop mid-wash jeans. She upped the retro ante with casual black-and-white running shoes.

All this to say? Holmes has been a fashion muse since her initial step-and-repeat. Keep scrolling for her best Y2K fashion moments. And stay tuned for more recreations in the coming years.

New York Film Festival, 1997

At the opening night of the 1997 New York Film Festival, Holmes attended The Ice Storm premiere in a black slip dress. The center of her midi-length dress was mesh, while the neckline and bottom hem were adorned with asymmetrical lace.

MTV New Year’s Eve Party, 1999

Just minutes before ringing in the new year, Holmes posed with Ananda Lewis in a sparkly crop top, dark-wash flared jeans, and a sleek leather coat. Her rectangular fashion glasses would fit right in with today’s style set.

Eyes Wide Shut Premiere, 1999

Always on board for an asymmetrical skirt, Holmes posed for photographers at the Eyes Wide Shut premiere in a lavender satin midi dress. From there, she layered a black cardigan with three-quarter length sleeves overtop.

Gossip Premiere, 2000

Holmes’ love for leather has stood the test of time. Back in April 2000, all eyes were on the actor in skinny leather trousers. She continued the all-black theme with a casual tank top, strappy sandals, and a Kate Spade top-handle bag.

MTV Movie Awards, 2000

Thanks to her a multi-color halter-neck dress, Holmes secured her spot on multiple best-dressed lists at the MTV Movie Awards. Her bejeweled slingback sandals increased the It girl energy.

X-Men Premiere, 2000

Holmes is a pro at elevated basics. Need proof? Here she is at the X-Men premiere in a plain white tee, a low-waisted snakeskin midi skirt, and another pair of strappy heels.

Tigerland Premiere, 2000

Between the polka-dot blouse, beige leather trousers, and a Louis Vuitton monogram clutch, Holmes’ outfit for the Tigerland premiere was Y2K fashion at its finest.

Out In NYC, 2001

On a day off from filming Dawson’s Creek, Holmes was snapped by the paparazzi in a button-up leather trench coat — the same topper from the 1999 NYE party. She kept a low-profile in jeans, chunky sneakers, and oval-shaped sunglasses.

Sundance Film Festival, 2003

At her inaugural Sundance Film Festival, Holmes modeled a striped cardigan alongside another Y2K must-have: a boho-chic white scarf.

Save The Music: A Benefit Concert, 2005

This elongated flouncy tunic styled with dark-wash jeans is only inches away from dress-over-pants territory.

Out In NYC, 2008

While running errands Manhattan, Holmes wore low-waisted boyfriend jeans with black ballet flats. She accessorized with a black Chloé hobo bag, statement sunglasses, and an of-the-moment fedora from Victor Osborne.