From winning multiple awards for her performance as Tanya McQuoid on The White Lotus to charming audiences with a Super Bowl commercial to starring alongside J.Lo in Shotgun Wedding, Jennifer Coolidge is having a resurgence for a new generation. But her biggest fans know that her extensive film career has left its mark since the ‘90s (Legally Blonde or Best in Show movie night, anyone?), complete with plenty of red carpet appearances and iconic fashion moments. While many of her characters have an affinity for the bold, Coolidge keeps things classic when it comes to her timeless looks offscreen—of course, with the occasional animal print thrown in.
Whether you want a crash course in the best Jennifer Coolidge fashion moments or are taking a walk down memory lane, keep reading for 18 standout looks the iconic actress has worn on and off the red carpet over the years.
Golden Globe Awards (2023)
Coolidge embraced sparkle for her triumphant night at the 2023 Golden Globe Awards, shining bright in a glittery black Dolce & Gabbana gown and a soft glam makeup look for her first Golden Globe win. It was almost as great as her onstage appearances as a presenter and to accept her award, which had fans dreaming of the idea of her hosting the show in the future.
'The White Lotus' Season 2 Premiere (2022)
At the much-anticipated premiere for The White Lotus Season 2, Coolidge stunned in a black lace Dolce & Gabbana number and simple strappy heels. Perhaps just as memorable as her look were the confident poses she struck on the red carpet alongside co-star Aubrey Plaza.
Emmy Awards (2022)
For the 2022 Emmy Awards, Coolidge dressed appropriately glam for her first-ever win in this green off-the-shoulder gown by Dolce & Gabbana. We couldn't think of a more perfect accessory than the well-deserved trophy.
Hasty Pudding Theatricals Parade (2023)
To no one's surprise and everyone's delight, Jennifer Coolidge was honored as the 2023 Hasty Pudding Theatricals Woman of the Year with a parade through Boston, plus a full weekend of fun events (her dolphin debut is not to be missed). For the occasion, she chose an outfit that couldn’t have been more true to her: a cheetah print coat and a fluffy pink hat.
Critics Choice Awards (2023)
Sweeping up yet another award for her role as Tanya in The White Lotus, Coolidge showed up to the 2023 Critics Choice Awards in one of her most elegant red carpet looks to date. She paired a black Dolce & Gabbana gown featuring a plunging neckline with black opera gloves, complete with jewels on both wrists.
'Like a Boss' Premiere (2020)
We love a monochromatic moment, and apparently, so does Jennifer Coolidge. The actress wore a green metallic Christian Siriano dress paired with a green hard-sided clutch to the premiere of Like a Boss in 2020.
'The White Lotus' Season 1 Premiere (2021)
To kick off her reign in The White Lotus, Coolidge embraced her character's flair for the dramatic with a leopard print gown with black star detailing on the waist.
Shotgun Wedding Premiere (2023)
For the premiere of Shotgun Wedding, Coolidge took to the red carpet in a long-sleeve black dress from Self-Portrait. As for shoes, she kept things classic with a pair of black pumps.
'Legally Blonde 2' Premiere (2003)
Following the smashing success of Legally Blonde, Coolidge reprised her role as Paulette Bonafonté alongside Reese Witherspoon's Elle Woods for the film’s 2003 sequel. For the premiere, the star wore a simple blue spaghetti strap dress, pairing it with a pendant necklace and a micro-clutch for a sweet early aughts moment.
Pre-Golden Globes Party (2004)
Nearly two decades before winning her first Golden Globe for The White Lotus, Coolidge proved herself to be an awards season life of the party in this silvery moment. From the sparkly knit bodycon dress to the smoky eye, this look is one we're definitely adding to our glam vision board.
'American Reunion' Premiere (2012)
Returning as Stifler’s mom for 2012's American Reunion (the fourth American Pie movie), Coolidge made a statement to celebrate the original film series' last hurrah. She looked stunning in an azalea strapless lace dress and glittering heels.
'American Wedding' Premiere (2003)
For the premiere of the third American Pie installment, Coolidge embraced timeless Hollywood glamour with her soft glam makeup look, eye-catching metallic silver dress, and strappy heels, adding a slouchy white purse for a pop of Y2K.
'A Cinderella Story' Premiere (2004)
While her wicked stepmother character, Fiona, in A Cinderella Story was known for her gaudy (yet iconic) fashion moments, Coolidge went a more subtle route with her red carpet premiere look. She sported a crochet see-through dress, and while this is from 2004, we can picture the statement going viral on TikTok today.
Canada's Walk of Fame Gala (2006)
Coolidge was a vision in Chanel at the 2006 Canada’s Walk of Fame Gala, where the luxury house was a sponsor. She stunned in a black tiered gown with chain straps and a strand of pearls, making a statement that would be just as chic in any era.
People's Choice Awards (2005)
At the 31st Annual People’s Choice Awards, Coolidge went the understated route with a lace-trimmed LBD and a pink overcoat. Of course, it wouldn’t be a 2000s look without a bit of logomania, which the American Pie star incorporated into her ensemble with a Coach logo print shoulder bag.
Beauty Industry Event in Los Angeles (2002)
Excuse us while we find a dupe for these oversized sparkly sunglasses. The actress wore this look to an event at The Chateau Marmont, and it’s giving everything Y2K.
'Down to Earth' Premiere (2001)
Coolidge was effortlessly chic in a simple black dress, red leather trench coat, and cross necklace at the premiere of Down to Earth, the 2001 remake of Heaven Can Wait. The understated yet colorful look is timeless, and we could definitely see that leather trench making street style waves today.
Press Event (2002)
This Jennifer Coolidge fashion moment embodies some of the chaotically iconic style choices celebrities were making in the early aughts, and we love the energy. From the abstract printed dress to the voluminous half-up hairstyle to the white crochet sweater, everything here feels very 2002.