Katie Holmes’s Style Transformation: From ‘Dawson’s Creek’ to the Infamous Cashmere Bra

Yes, that is Dawson himself, James Van Der Beek, you spy behind Holmes on the Emmys red carpet. While we adore her cap-sleeve white embroidered gown and simple strands of pearls (pins to wedding Pinterest board, immediately), the rosette-covered handbag is a bit much.

OK, so this outfit was likely put together by the show’s stylist, but still, we’ve spotted the actress wearing something very similar to this exact combo many, many times in the 22 years since.

Not even MTV’s New Year’s Eve Party could break Holmes and her beloved jeans apart. (Though we still give her festive points for the subtly sparkly top.)

With just a few tweaks, Holmes’s early red-carpet style could pass for a trendy outfit 2021.

Maybe it was the influence of Joey Potter’s basic flannels and loose jeans, but Holmes has long been a fan of taking simple, casual wardrobe basics (like a plain white tee) and dressing them up just so.

We’re pretty sure every young female celeb in the early 2000s wore basically this same outfit—flirty, cap-sleeve top, low-rise bootcut jeans and pointy-toe boots—to multiple red carpet events. What a time to be alive.

The UGGs! The low-rise, distressed jeans! The bucket hat! The Matrix-style sunglasses! Holmes has packed so many trends in one outfit, we barely even noticed the gorgeous mountain views and sunset behind her.

Does anyone else remember when Victoria Beckham and her husband moved to L.A., where they struck up a long-lasting friendship with the newly married Holmes? Well, it appears Posh Spice’s sensibilities may have rubbed off on the actress.

Look, the 2000s were a confusing time in fashion for everyone. While we love a good oversize knit-and-leggings combination, this one doesn’t quite hit the mark. (Though there are number of celebs who’d currently approve of that shaggy bob haircut.)

Queen of Easy Basics, Holmes knows that a strong pair of jeans can make the outfit. But what really stands out is that hot pink bra, perhaps a nod to the beginning of a more experimental fashion phase.

Both Holmes’s and Suri’s outfits here are all about the accessories. A wide-brim hat, super-size sunnies, equally oversize tote and slouchy knee-high boots for mom, and coordinating bright pink backpack, sneakers and arm cast for her 7-year-old daughter.

It appears we’re late to pick up on Holmes’s style renaissance, which appears to have started long before we realized. She rocked this pleated leather and silver knit ‘fit for an appearance on Good Morning America to promote her directorial debut, a short documentary for EPSN on Olympic gymnast Nadia Comăneci.

Now is when we start to see the actress really honing in on her sartorial sweet spot: turning comfy basics into elevated fashion statements.

Who would’ve guessed a slouchy denim jumpsuit would look so chic when paired with a tailored gray blazer, black pointy-toe pumps and a swipe of red lipstick?

Holmes doesn’t often sport prints, but we can’t get enough of the mismatched stripes and florals she wore to the Zimmermann runway show during Fashion Week.

This is not the simple top and jeans of yesteryear. Holmes attended multiple Fashion Week events (including the Ulla Johnson runway show pictured above), wearing one stunning ensemble after another.

While it was certainly a thrill to see Holmes experimenting with bolder, more fashion-forward ensembles pre-quarantine, she’s truly at her best when rocking the basics, and it seems she may feel her best in them as well—why else would someone choose to sport a plain white tee, sweatpants and tall socks for date night with their new beau?

In March 2021, Holmes stepped out in New York City alongside her boyfriend, Emilio Vitolo. The actress wore an all-black outfit, featuring a fur-trimmed leather bomber jacket, black jeans and a pair of leather boots. She completed the look with a houndstooth bag, hoop earrings and a black face mask from Evolvetogether.

You keep on doing you, Katie.

KELLY RIPA’S STYLE TRANSFORMATION OVER THE YEARS