At the 1998 premiere of Deceiver, the it girl looked cozy in a cream-colored fur jacket, grey sweater and black pin-striped skirt paired with black opaque tights and lace-up ballet flats.
At the 52nd Annual Directors Guild Awards in 2000, Sevigny rocked a baby pink ensemble with a multi-colored silk scarf around her neck.
Sevigny was simultaneously Hollywood glam and downtown cool at the 2002 Vanity Fair Oscar Party in a white Grecian-inspired gown with a gold pendant necklace and gold clutch bag.
The actress looked darling in an '80s-inspired strapless dress and black velvet chocker at the Fashion Group International’s 21st Annual Night of Stars in 2004.
Fresh faced at ICP’s 21st Annual Infinity Awards in 2005, Sevigny wore a sexy floral maxi dress with a low square-cut neckline and ruffled bodice.
The actress wore a ruffled, belted LBD to a fundraiser in 2005.
At the 2006 Cannes Film Festival, Chloe wore a flirty and fun look on the red carpet. Her black and cream graphic-print fringe dressed was paired with a pair of simple black peep-toe wedges and a gold link necklace.
Chloe Sevigny arrived to the 2007 HBO Golden Globes After Party rocking another gorgeous graphic dress.
In a cut-out white fringe midi dress, the actress looked chic on her way to the 2007 Vanity Fair Oscar Party.
The actress celebrated her collaboration with Opening Ceremony in 2008 wearing a school girl-inspired look from the line.
Sevigny turned heads on the red carpet of the 61st Annual Emmy Awards dressed in a gorgeous gown by Issac Mizrahi. The polka dot-covered sheer gown stayed true to the actress' quirky style, but was appropriately glamorous for the occasion.
Ready to dance the night away, the actress wore a bold and edgy turquoise Proenza Schouler mini dress and black sky-high platform sandals to the 2010 Met Gala.
Chloe Sevigny showed a little skin at HBO’s Big Love premiere in 2011 in super chic blue floral Rodarte dress paired with red and gold cutout sandals and matching red lip.
At the New York premiere of Orange is the New Black, the actress wore a sparkly navy crew-neck sweater, high-waisted printed shorts and white patent oxfords.
Sevigny went matchy-matchy in an orange suede Chloe mini-dress paired with orange strappy sandals, at the Cartier 100th anniversary of their emblem La Panthere De Cartier in 2014.
At the LACMA 2015 Art+Film Gala, Sevigny was glowing in a lace bright yellow printed Gucci gown. She kept her accessories very minimal by only wearing baby blue teardrop earrings, a yellow crystal ring and burgundy clutch bag.
The actress stunned on the red carpet at the New Yorkpremiere of her film #Horror in a pink and black Proenza Schouler dress. This dramatic number featured a high neck, thigh-high split and scandalous hip cutout.
At a New York screening of her newest film Love & Friendship, the actress looked simply angelic in a Peach chiffon Prada gown. The gown featured a white embellished collar and cuffs and a multi-colored graphic on the the bodice.
At the 2017 Sundance Film Festival's premiere of ' Golden Exits, Chloe debuted her signature vintage style as she posed for pictures in a brown suede duster coat over a vintage print dress. She completed her look with black leggings, leather oxfords and handbag.
The actress/director debuted a 60's inspired gold and green sequin Miu Miu mini dress at the Sundance "Beatriz At Dinner" premiere. She added a bit of edge to her look with a pair of black motto boots and black leather handbag.
Chloe looked adorably hot in a red Miu Miu mini dress that featured bow-adorned shoulder detailing at the amfAR New York Gala 2017. She completed her look with a pair of black bejeweled mules, embellished black clutch bag and black chocker necklace.
While attending the Metrograph Theater 1st Year Anniversary Party, the actress donned a silver floor-length J.W. Anderson turtleneck dress. Keeping her accessory pairings simple she opted for a black leather chain strap bag and gold statement earring by the designer.
Chloe Sevigny attends The Hollywood Reporter 2018 Sundance Studio at Sky Strada, Park City on January 20, 2018 in Park City, Utah. Photo courtesy of Getty Images.
Chloe Sevigny attends the 'Lizzie' Premiere during the 2018 Sundance Film Festival at Park City Library on January 19, 2018 in Park City, Utah. Photo courtesy of Getty Images.
Chloe Sevigny arrives at the Gucci show during Milan Fashion Week Fall/Winter 2018/19 on February 21, 2018 in Milan, Italy. Photo courtesy of Getty Images.
Chloe Sevigny attends Metrograph 2nd Anniversary Party at Metrograph on March 22, 2018 in New York City. Photo courtesy of Getty Images.
Chloe Sevigny attends the "Last Days Of Disco" 20th anniversary screening at Walter Reade Theater on May 24, 2018 in New York City. Photo courtesy of Getty Images.
Chloe Sevigny attends the Gitano NYC preview celebration on June 21, 2018 in New York City. Photo courtesy of Getty Images.
Chloe Sevigny walks the red carpet ahead of the "L'Annee Derniere a Marienbad" screening during the 75th Venice Film Festival at Sala Giardino on September 5, 2018 in Venice, Italy. Photo courtesy of Getty Images.
Chloe Sevigny, wearing Fendi, attends Moet & Chandon and Virgil Abloh New Bottle Collaboration Launch at The New Museum on October 16, 2018 in New York City. Photo courtesy of Getty Images.