Michelle Williams' Stunning Style Evolution

While the entire cast of "Dawson's Creek" has changed quite a bit, no one has had a stunning style evolution quite like Michelle Williams. For six seasons, Williams played Jen Lindley — a complex character with a troubled past — so well that it didn't just launch her career, but allowed Williams to secure roles that the other cast members just couldn't. For example, just two years after "Dawson's Creek" wrapped, Williams earned her first Academy Award nomination for her heart-wrenching portrayal of Alma Beers Del Mar in the 2005 critically acclaimed film, "Brokeback Mountain."

But when Williams wasn't playing offbeat characters and making audiences cry with her nuanced and beautiful work, she was in the midst of a style evolution — and we're not just talking about her pixie cut that will inspire your next super short haircut. Growing up in the public eye, Williams went from a 1990s teenager desperately in need of a stylist to a fashion powerhouse. So much so, that she has become the muse of Nicolas Ghesquière, the artistic director behind Louis Vuitton. "I first design from instinct, an intuition I want to express something," Ghesquière told Elle UK in 2019. "So I draw, then at some point [I start] questioning if Michelle, for example, would love this look."

While becoming a muse for one of the top designers in the world is definitely extraordinary, it wasn't always this way for Williams. In the early days, she navigated her fashion choices without such heavyweights on her side, making her style evolution exciting to witness.

In 1998, Michelle Williams attended an event at Mann's Village Theatre, embracing everything that went with being a teenager in the 1990s, including a blasé pout. When it came to dressing up, a shift dress was always the safest bet, and there was no need for jewelry beyond a choker — in fact, even a satin ribbon would do. While chokers were one of the summer's hottest '90s redux jewelry trends back in 2023, for those of us who came of age in the 1990s, it's something we'll never truly surrender. While the open-toe heels are definitely a nice touch, had Williams gone for a pair of Doc Martens, that really would have clinched the look.

For her appearance at the GLAAD Media Awards in 2000, Michelle Williams rocked a gray menswear outfit that will make you want to raid your boyfriend's closet. Completing the look with an iconic white T-shirt instead of a button-down Oxford-style shirt gives this an extra casual chic vibe. Another great choice is pairing the gray suit with red, open-toe sandals, giving the entire ensemble just a pop of color. While both Katie Holmes and Meredith Monroe look great in their own right in their very on-trend dresses for the time, Williams brings major sultry sex appeal to the equation.

In 2005, on the cusp of major stardom, Michelle Williams attended the "Brokeback Mountain" New York City premiere wearing an adorable off-white satin dress with black lace at the bust and a matching ribbon around the waist to create a lovely contrast. Williams also chose to go with black accessories for the premiere, with a black clutch and black heels. But what really stands out is that it appears that Williams is wearing incredibly minimal makeup (if any at all) — and this is long before Pamela Anderson made waves by going makeup-free to events. Of course, Williams' natural beauty doesn't need to be gussied up, but it's an interesting choice for attending her own premiere.

Just one year after the "Brokeback Mountain" premiere, Michelle Williams did a 180 when attending the 2006 Academy Awards. Nominated for Best Supporting Actress, Williams wore a marigold gown by Vera Wang, with impeccable details throughout and just enough of a train for dramatic effect. She also wore a diamond necklace and carried a small sparkly clutch. She had her blond locks swept to the side, and proved that night she'd mastered the art of the red lip, evoking major old Hollywood glamour. Even now, almost 20 years later, this dress still shows up on the best Oscar gowns lists of all time.

For the 2010 premiere of "Blue Valentine," Michelle Williams chose to go playful with her dress choice, opting for sparkles, bows, and tiered ruffles. The mini dress, designed by Azzaro, was in stark contrast to the plot of "Blue Valentine," making it not only an interesting choice, but also proving that Williams has no interest in being one of those celebs who take method dressing to the next level when promoting her films. By 2010, she'd already entered her platinum pixie cut era, and this is one of the many incarnations of the look she'll flawlessly pull off in the years to come.

In 2015, for the InStyle Awards at the Getty Center, Michelle Williams leaned into her edgy side with a black leather embellished mini dress and black leather boots. Although she'd already solidified herself as being very much the queen of pixie cuts, she grew her hair out just long enough to have a wispy lob. Pairing the lob with curtain bangs immediately put Williams in the coveted category of celebs who have rocked chic curtain bangs and nailed the look. It's the ultimate hair inspo that looks so good, you just might be willing to give these bangs a try.

For Michelle Williams, 2020 was a big year — well, before the pandemic kicked in, of course. Not only did she win the Primetime Emmy Award and Golden Globe Award for Best Actress in a Television Miniseries for her performance as Gwen Verdon in FX's miniseries, "Fosse/Verdon," but she also got to wear a Greek goddess-inspired dress by Louis Vuitton to the Golden Globes. While orange and baby blue silk may seem like an odd pairing, Williams had already proven that she can pull off colors that others just can't, as evidenced by the iconic marigold Vera Wang gown. Williams' platinum chin-length bob with subtle finger waves brought the entire look together.

Thanks to her relationship with Nicolas Ghesquière, Michelle Williams wears a lot of Louis Vuitton, so when she attended the 3rd Annual Academy Museum Gala at the Academy Museum of Motion Pictures in December 2023, she was in LV again. However, in stark contrast to the billowy cut and bright colors of the LV look she wore in 2020 to the Golden Globes, this navy gown was comprised of sequins and layers of metallic fringe, giving it a futuristic vibe. In 2023, Williams also went back to her super-short pixie, giving her the opportunity to wear an elegant diamond cuff on her ear and have it be noticed.

When Michelle Williams attended the Met Gala in 2024 for the fifth time, celebrating "Sleeping Beauties: Reawakening Fashion," she really brought her A-game. Wearing a custom white mini dress by Chanel with puffed sleeves and a long, dramatic train, Williams literally looked like a dream. To complete the look and stick to the theme without going overboard, Williams only wore a ring and what appears to be a diamond headband on her dyed-pink hair. She looked absolutely ethereal and, in doing so, proved she understood the assignment.

In October 2025, Michelle Williams was spotted on her way to the Lacoste show during Paris Fashion Week. While monochromatic looks make for a winning outfit on lazy days, there's absolutely nothing lazy about Williams' monochromatic ensemble. Between the high-waisted shorts, oversized blazer, matching heels, and her sleek bob, Williams looks like she's on her way to close a major deal and topple the patriarchy at the same time. Even her sunglasses are serving in a way that says this is a woman who has arrived, but she's also only getting started.