Kelly Osbourne Rediscovers Dress She Wore for Special Red Carpet Moment with Amy Winehouse 4 Years Before Her Death

The two attended an awards ceremony in 2007 before Winehouse died on July 23, 2011

NEED TO KNOW

• Kelly Osbourne reflected on her friendship with Amy Winehouse while looking through her closet archives in a new video
• The reality star was close friends with the British “Valerie” singer, who died at 27 from accidental alcohol poisoning in 2011
• Osbourne also recently mourned the loss of her father, Ozzy Osbourne, who died in July 2025

Kelly Osbourne keeps her fondest memories close by.

In a video shared to Hello! Canada‘s Instagram, the reality star, 41, uncovered some personal memorabilia ahead of her move to her “new little cottage in the woods” and shared the backstory behind a designer dress she wore for an event with Amy Winehouse four years before she died in 2011.

At the end of the clip, Osbourne showed a white and black polka-dot dress by Oscar de la Renta, describing the piece as her “most favorite” that has meant “so much” to her after all these years. Osbourne’s pictured in the outfit at Elle‘s 2007 Style Awards, where they were both honored.

Winehouse died on July 23, 2011, from accidental alcohol poisoning. She was 27 years old.

Winehouse was discovered lifeless inside her London townhouse by her bodyguard, and was pronounced dead by the time emergency services arrived. Several large bottles of vodka were found in her room at the time of her death, according to forensic investigators at the time.

In 2019, Osbourne mourned the tragic loss of her close friend on the anniversary of her death, writing on Instagram, “Not a day goes by that I don’t miss you #lul.” According to the Daily Beast, the two spoke over the phone the night before Winehouse died inside her Camden townhouse in London.

Most recently, Osbourne lost her father, Ozzy Osbourne, who died on July 22, 2025, at age 76.

“It is with more sadness than mere words can convey that we have to report that our beloved Ozzy Osbourne has passed away this morning,” the Osbourne family told PEOPLE in a statement. “He was with his family and surrounded by love. We ask everyone to respect our family privacy at this time.”

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This summer, close to the one-year anniversary of the Black Sabbath rocker’s death, Osbourne got a tattoo of his signature glasses inked in his honor.