Gwyneth Paltrow Stuns in a Bold Red Prada Dress at 2016 Hamptons Paddle & Party For Pink

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In August 2016, Cruel Doubt actress Gwyneth Paltrow hosted the 2016 Hamptons Paddle & Party For Pink held in Bridgehampton, New York. The event was a breast cancer benefit—could this be why Gwynnie opted for a daring look that featured major sideboob?

Gwyneth Paltrow leaves her blonde hair down in a red Prada dress on stage at a breast cancer awareness eventGwyneth Paltrow leaves her blonde hair down in a red Prada dress on stage at a breast cancer awareness event (Credit: IZZY / Rob Rich / WENN)

The 43-year-old actress hosted the benefit, which raised over $1.75 million for the non-profit Breast Cancer Research Foundation.

A Look Back at Gwyneth Paltrow’s Early Career: Cruel Doubt with Blythe Danner

As we admire Gwyneth Paltrow’s bold fashion choice at the 2016 Hamptons Paddle & Party For Pink, it’s worth revisiting one of her earlier roles that showcased her acting talents alongside her mother.

Twenty-four years earlier, she portrayed Angela Pritchard in the 1992 television miniseries Cruel Doubt. She co-starred with her mother, Blythe Danner, who portrayed Bonnie Von Stein.

When the film was broadcast in two parts on NBC in the United States and on CTV in Canada on May 17 and May 19, 1992, Gwyneth Paltrow was 19 years old. She celebrated her 20th birthday on September 27, 1992.

In the miniseries "Cruel Doubt," Blythe Danner took on the role of Bonnie Von Stein, while her daughter, Gwyneth Paltrow, portrayed Angela PritchardIn the miniseries “Cruel Doubt,” Blythe Danner took on the role of Bonnie Von Stein, while her daughter, Gwyneth Paltrow, portrayed Angela Pritchard (Credit: NBC)

Cruel Doubt is an adaptation of Joe McGinniss’ true crime book, which you can buy on Amazon.

The book meticulously chronicles the tragic murder of Lieth Von Stein in 1988, committed by his stepson, Chris Pritchard, along with two accomplices, James Upchurch and Gerald Neal Henderson.

Blythe Danner was diagnosed with oral cancer in 2018. She revealed her battle with adenoid cystic carcinoma, a rare form of oral cancer, in 2022. Danner underwent treatment and surgery and has spoken about how this experience has deepened her connection to her late husband, Bruce Paltrow, who also died from oral cancer in 2002.

Gwyneth Paltrow’s Style Evolution: From Cruel Doubt to Present

Returning to the present, Gwyneth’s daring fashion choices at the breast cancer benefit event prove her style evolution has been as captivating as her career.

Gwyneth Paltrow confidently speaks at the 2016 Hamptons Paddle & Party For Pink, showcasing her bold red Prada dress with side cutoutsGwyneth Paltrow confidently speaks at the 2016 Hamptons Paddle & Party For Pink, showcasing her bold red Prada dress with side cutouts (Credit: IZZY / Rob Rich / WENN)

Gwyneth Paltrow’s Red Prada Dress: A Risky Yet Memorable Choice

The Goop founder showed skin and more in her red Prada halter maxi dress, trimmed with pink piping and a bow at the back. Her red dress featured thin straps, an ankle-skimming hemline, and a shapeless structure.

Gwyneth Paltrow and Tracy Anderson attend the 2016 Hamptons Paddle & Party For Pink at Fairview on Mecox BayGwyneth Paltrow and Tracy Anderson attend the 2016 Hamptons Paddle & Party For Pink at Fairview on Mecox Bay on August 6, 2016, in Bridgehampton, New York (Credit: IZZY / Rob Rich / WENN)

At least no one could say she wasn’t dressed for the occasion. The Royal Tenenbaums star also opted for a no-makeup look, tousled blond hair, and an exposed bikini tan line.

Gwyneth Paltrow stuns in a vibrant red Prada dress paired with black Gianvito Rossi sandals at the 2016 Hamptons Paddle & Party For PinkGwyneth Paltrow stuns in a vibrant red Prada dress paired with black Gianvito Rossi sandals at the 2016 Hamptons Paddle & Party For Pink (Credit: IZZY / Rob Rich / WENN)

Gwyneth Paltrow’s Footwear Choice: Gianvito Rossi’s ‘Crissy’ Sandals

She finished her ensemble with Gianvito Rossi’s clunky suede “Crissy” sandals.

Gwyneth Paltrow completes her look with black Gianvito Rossi "Crissy" suede sandalsGwyneth Paltrow completes her look with black Gianvito Rossi “Crissy” suede sandals (Credit: IZZY / Rob Rich / WENN)

While the shoes are stunning on their own, they didn’t quite complement Gwyneth’s beach-ready look. See how Adriana Lima successfully styled these Gianvito Rossi ‘Crissy’ sandals.

Black Gianvito Rossi "Crissy" Suede Ankle-Tie SandalsBlack Gianvito Rossi “Crissy” Suede Ankle-Tie Sandals, $795