Best Celebrity Fashion Moments of the Week: Oprah Winfrey and Taraji P. Henson Shine and More Must-See Looks

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The Color Purple and its stars are having a moment on the big screen and in the fashion department. Earlier this week, Taraji P. Henson, who plays one of the musical adaption’s main characters, rejoiced as the film won Best Ensemble at the 2023 Critics Choice Association’s Celebration of Cinema & Television for Black, Latino & AAPI Achievements.

While posing in the IMDb Exclusive Portrait Studio, the actress wowed in a PatBo dress and silver heels.

As for Oprah Winfrey, who made her film debut in the 1982 original adaptation of Alice Walker’s Pulitzer Prize-winning novel, she celebrated at the Academy Museum Gala in a Dolce & Gabbana dress with purple sapphire drop earrings from Hamilton Jewelers.

Taraji P. Henson and Oprah Winfrey aren’t the only stars celebrating fashion success this week. The Messenger searched social media, red carpets and the hottest parties to see who pulled off winning looks. See who deserves a round of applause for their eye for style in our weekly roundup of the best celebrity fashion moments.

Best holiday top: Hailee Steinfeld

Hailee Steinfeld celebrates the holiday season at Amazon Small Business’ holiday event in Los Angeles
Hailee SteinfeldCibelle Levi for Amazon

While celebrating the holiday season at Amazon Small Business’ holiday event in Los Angeles, Hailee Steinfeld had some fun in the fashion department with her David Koma two-piece set and Jessica Rich set.

Best fashion surprise: Billie Eilish

Billie Eilish attends Claudia Sulewski's launch of sustainable bodycare brand CYKLAR at Solawave House on December 05, 2023 in Los Angeles, CaliforniaBillie Eilish attends Claudia Sulewski's launch of sustainable bodycare brand CYKLAR at Solawave House on December 05, 2023 in Los Angeles, California
Billie EilishJohn Sciulli/Getty Images for CYKLAR

While Grammy winner Billie Eilish likes to follow her own fashion rules with dark colors and even some sweatshirts, the singer switched things up while attending Claudia Sulewski’s launch of sustainable bodycare brand CYKLAR. Eilish sported a Gucci baseball cap with a Marine Serre side-laced shirt.

Best date night style: Chrissy Teigen

Chrissy Teigen elevates her Old Navy pajama pants into a glam date night look, en route to Uchi restaurant with husband John Legend.Chrissy Teigen elevates her Old Navy pajama pants into a glam date night look, en route to Uchi restaurant with husband John Legend.
Chrissy TeigenSara Jaye Weiss

Craving some relatable style? Chrissy Teigen is here to help. While stepping out for a date night with John Legend, the best-selling author opted to stay cozy in Old Navy pajama leggings with a long overcoat from the brand.

Best boots: Dixie D’Amelio

Dixie D’Amelio attends iHeartRadio 102.7 KIIS FM's Jingle Ball 2023 Presented by Capital One at The Kia Forum on December 01, 2023 in Los Angeles, California.Dixie D’Amelio attends iHeartRadio 102.7 KIIS FM's Jingle Ball 2023 Presented by Capital One at The Kia Forum on December 01, 2023 in Los Angeles, California.
Dixie D’AmelioJesse Grant/Getty Images for iHeartRadio

The D’Amelio Show star Dixie D’Amelio kicked off the holidays at KIISFM’s iHeartRadio Jingle Ball in a Raisa Vanessa pink cocktail dress with matching Versace x Dua Lipa metallic boots. She completed her look with Emma Pills hoop earrings before enjoying a night of music.

Best onesies: Patrick and Brittany Mahomes

Patrick and Brittany Mahomes enjoy the holiday season.Patrick and Brittany Mahomes enjoy the holiday season.
Patrick & Brittany MahomesBrittany Mahomes/Instagram

‘Tis the season for ugly sweaters and holiday onesies. Before getting game-day ready, Kansas City Chiefs quarterback Patrick Mahomes and his wife Brittany attended a Christmas party in matching Rudolph jumpsuit onesies from Shark Tank favorite Tipsy Elves.

Best kids style: True and Tatum Thompson and Dream Kardashian

True and Tatum Thompson pose with Dream Kardashian.True and Tatum Thompson pose with Dream Kardashian.
True Thompson, Tatum Thompson & Dream KardashianKhloe Kardashian/Instagram

Before watching a classic holiday movie this season, Khloe Kardashian decided to dress her kids and niece in cozy Zip N’ Bear pajamas. “The MOST magical time of year!!!” The Kardashians star wrote on Instagram. “We are in the Christmas spirit in our Christmas pajamas and our Christmas dance moves.”

Best menswear: Tyler Cameron

Tyler Cameron attends Louis Vuitton’s cocktail event in Miami.Tyler Cameron attends Louis Vuitton’s cocktail event in Miami.
Tyler CameronDarian DiCianno/BFA

Goodbye frigid New Zealand and hello sunny Miami. After winning Season 2 of Special Forces, Tyler Cameron proved he’s also winning in the fashion game as he stepped out for Louis Vuitton’s cocktail event. His classic white sneakers matched his jacket from Louis Vuitton perfectly.

Best pop of pink: Kathy Hilton

Everything is looking hunky dory in the fashion department for This Is Paris star Kathy Hilton. Her alice + olivia pink dress was the perfect match to her holiday tree. As she shared on Instagram, “It’s starting to look a lot like Pinkmas!”

Best red-hot dress: Maren Morris

Maren Morris attends Variety's Hitmakers presented by Sony Audio on December 02, 2023 in Hollywood, California.Maren Morris attends Variety's Hitmakers presented by Sony Audio on December 02, 2023 in Hollywood, California.
Maren MorrisMatt Winkelmeyer/Variety via Getty Images

Before accepting her award at Variety‘s Hitmakers event presented by Sony Audio, Maren Morris turned heads in her red-hot Vivienne Westwood gown styled by Dani Michelle. “Thank you @Variety for giving me the award of Changemaker of the Year,” the “My Church” singer wrote on Instagram. “The changes are still coming but I’m honored to not be on this journey alone.”

Best sparkling set: Serena Pitt

Serena Pitt attends iHeartRadio 102.7 KIIS FM's Jingle Ball 2023 Presented by Capital One at The Kia Forum on December 01, 2023 in Los Angeles, California.Serena Pitt attends iHeartRadio 102.7 KIIS FM's Jingle Ball 2023 Presented by Capital One at The Kia Forum on December 01, 2023 in Los Angeles, California.
Serena PittJesse Grant/Getty Images for iHeartRadio

Bachelor in Paradise star Serena Pitt sparkled and shined while attending KIISFM’s iHeartRadio Jingle Ball. With help from stylist Lisa Marie Cameron, the reality star turned heads in her NBD set, FEMME heels and Ettika earrings. And yes, she was able to dance the night away to Niall Horan and Olivia Rodrigo.

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