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 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.

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’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.

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’s Footwear Choice: Gianvito Rossi’s ‘Crissy’ Sandals
She finished her ensemble with Gianvito Rossi’sclunky suede “Crissy” sandals.

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.
