Chloë Sevigny's Most Effortlessly Cool Looks From The '90s And Early '00s
Chloë Sevigny was catapulted to "It Girl" status in the '90s, entering the scene with a unique look and an offbeat sense of style. Her career kicked off with fashion spreads in magazines like Sassy and i-D, while her role in the controversial 1995 film "Kids" put her solidly on the map of mainstream fame. Even though she's populated mood boards alongside Alexa Chung and indie sleaze queen Drew Barrymore, the Massachusetts native isn't convinced of her title as a style icon. "I'm pretty wacky," she told Elle in 2026. "When people say I have such good style, I'm like, 'Do I?'"
A look through Sevigny's '90s and '00s wardrobe uncovers the easy coolness she's known for, full of early '00s outfits we'd actually wear today. While her lookbook may feel eclectic at times, she's balanced messy and edgy elements of grunge with trendy and high-fashion pieces. "I was just teetering around," she said of the era. "It was quite grungy and carefree, whereas now things seem more polished." Overall, the sense of style she cultivated easily translates into the slouchy indie sleaze aesthetic that followed in the late 2000s and 2010s. With all this in mind, it's easy to see why Sevigny's fashion from early in her career has been so enduring.
She stunned in a lacy black dress and dark lip
Chloë Sevigny showed off her distinct sense of style at a 1998 event hosted by The Fashion Group. The "Boys Don't Cry" star was pictured wearing a black, ankle-length gown from an unknown designer. The silhouette seems to have taken inspiration from Chinese fashion, featuring a mandarin-style collar and short sleeves, as seen in traditional qipao gowns, and a lacy overlay, especially visible at the untrimmed hem. The young star completed the ensemble with a fur coat and a vampy lip stain, keeping her overall beauty on the minimal side.
Chloë went for an eclectic, layered look at a 1999 movie premiere
Chloë Sevigny was repping her eclectic sense of style back in 1999 when attending the premiere of the sci-fi horror film "Existenz." She wore a long blue shirt over a sheer white dress from unknown brands, pairing the combination with knee-high leather boots and a classic tan trench coat. The "Boys Don't Cry" actor wore her hair in a collarbone-length cut with bangs across her forehead, allowing her blond tresses to take on a slightly messy look that would become a staple of the indie sleaze aesthetic.
The star played into tropical Y2K vibes at the SAG Awards
Chloë Sevigny was a tropical dream at the Screen Actors Guild Awards in 2000, wearing a loose, sheer dress that spoke to Y2K's beachy influence. The Yves Saint Laurent piece featured a patterned silhouette of tropical flowers and a boatneck that gave way to flowy, short sleeves. She wore her hair in a sleek bob with side-swept bangs and added a matching red lip. Sevigny was neither the first nor the last celeb to infuse Y2K's kitchiness with beachy vibes, but she definitely delivered her cool-girl energy.
Chloë put a casual spin on menswear at a nominees luncheon
The casual side of Chloë Sevigny's style was on full display during the Academy Awards Nominees Luncheon. The actor wore a pair of grey, tailored shorts with a white blouse adorned with navy cuffs and ruffles across the front. She styled the menswear-inspired pieces with a casually undone tie and a gold necklace, keeping her beauty simple with a bob tucked behind her ears, slim brows, and a glossy lip. Sevigny's nonchalant approach to tailored pieces reflects the effortless, carefree vibe she cultivated very early on in her career.
She added a leather jacket to her Old Hollywood ensemble
Chloë Sevigny gave a nod to Old Hollywood glam at the 2000 Academy Awards and the Vanity Fair after-party. When speaking with Vogue, the Massachusetts native explained that she chose the low-cut Alber Elbaz for Yves Saint Laurent dress with intention. "I knew that the photo would probably come up for the rest of my life, so I wanted to do something more timeless," she said. For the after-party, she added a leather jacket and piled on bracelets to give her glamorous look a sense of edge.
She leaned into menswear at the Vogue Fashion Awards
Chloë Sevigny's lookbook is no stranger to androgyny, and the "Big Love" actor opted for menswear at the 2000 VH1 Vogue Fashion Awards. She wore an all-black suit from Balenciaga consisting of a ruffled blazer with three-quarter sleeves, accessorizing with brown, pointed-toed heels and a statement brooch. Her hair was styled into a middle-parted bob, while a swipe of red lipstick and thin brows to complete the look. She was absolutely fierce posing alongside French designer and long-time collaborator Nicolas Ghesquière, who brought her to the event.
Chloë was cool and casual in a corset and jeans back in 2002
Chloë Sevigny embodied her effortless "It Girl" persona at the premiere of "Human Nature" in 2002. She combined a corset-style top with a pair of bootcut jeans, completing the outfit with a drawstring handbag and pointed-toed heels. Sevigny's styling definitely speaks to trends of the era, with both Mýa and Christina Aguilera sporting a corset in the iconic "Lady Marmalade" music video, while bootcut jeans ruled the early 2000s. At the same time, the outfit is simple enough to inspire anyone styling a trendy corset top today.
She was dressed for the cold at the 2003 Sundance Film Festival
Chloë Sevigny looked like she could've stepped straight out of Sofia Coppola's "The Bling Ring" when spotted on the street during the 2003 Sundance Film Festival. She wore a grey, loose-fitting dress under a black furry bomber jacket, accessorizing with over-the-knee knit socks, fur-lined boots seemingly from Tecnica, and a pair of oversized sunglasses. She wore her hair casually styled in a middle-part with loose waves at the ends. The completed outfit definitely captures the era's love affair with fur and its proclivity toward plenty of layers.
Her bleached brows at the Seabiscuit premiere are still in vogue today
At the 2003 "Seabiscuit"s premiere, Chloë Sevigny channeled simple elegance while tapping into a beauty trend that has since come back in style. The actor posed in a white, trumpet-shaped gown, styling the piece with a pair of silver heels and middle-parted straight hair. She also took inspiration from icons like Madonna and Linda Evangelista by sporting bleached brows with messy eyeliner. The lightened eyebrows gave an unexpected edginess to the entire ensemble, making for another effortlessly cool look from Sevigny.
Chloë spiced up an office-inspired outfit with a chic miniskirt
Chloë Sevigny once again turned heads in a tailored 'fit when pictured at the 2003 Toronto International Film Festival. She was pictured at a screening of "Dogville" wearing a striped button-up with a popped collar and sleeves rolled up to the elbows. She styled the classic officerwear top with a gray miniskirt and shiny heels. As for beauty, she wore a middle-parted ponytail and a swipe of pink lip gloss. This look, alongside the other menswear entries in her lookbook, demonstrates Sevigny's longstanding and evolving relationship with chic haberdashery.