Kelly Osbourne is taking a heartfelt trip down memory lane.
The television personality recently rediscovered a dress that instantly brought back memories of one of her closest friends, the late Amy Winehouse, more than a decade after the Grammy-winning singer’s death.
Osbourne reflected on the special friendship after coming across a black-and-white polka-dot Oscar de la Renta dress while packing up her belongings ahead of a move to what she described as her “new little cottage in the woods.” The gown was one she wore to the 2007 Elle Style Awards in London, where she and Winehouse were both honored.
A Friendship Built on Support Through Life’s Highs and Lows
Osbourne and Winehouse shared a close bond that stretched across several years before the singer’s death in July 2011.
According to The List, the pair first met at a club, where Winehouse later joked during a 2007 appearance on “The DL Show” that she introduced herself by telling Osbourne, “I love your tattoos.” The lighthearted encounter quickly turned into a lasting friendship.
The two reportedly became especially close as they navigated similar struggles with addiction and sobriety. During one difficult chapter in Osbourne’s life, Winehouse helped her through a painful breakup. In her 2017 memoir, “There Is No F—ing Secret: Letters From a Badass Bitch,” Osbourne also revealed the two even lived together for a period of time.
Their friendship was marked by mutual support in happier moments as well. According to People, Winehouse attended Osbourne’s stage debut in the London production of “Chicago” in 2007 to cheer her on from the audience.
Their final conversation has remained one of Osbourne’s most difficult memories. Per The List, citing the Mirror, the friends spoke on the phone for about an hour the night before Winehouse died. After learning of her death, Osbourne said she was left stunned because Winehouse had seemed “absolutely fine.”
Winehouse died on July 23, 2011, at age 27 from accidental alcohol poisoning after being found unresponsive in her London home.
Kelly Has Continued Honoring Amy’s Memory
Although more than a decade has passed, Osbourne has never stopped celebrating her friend’s life.
On the anniversary of Winehouse’s death in 2019, she shared a simple but emotional Instagram tribute that read, “Not a day goes by that I don’t miss you #lul.”
The following year, according to The List, Osbourne posted previously unseen photos of herself and Winehouse together at a concert in London, saying the images made her happy to revisit. She later shared another heartfelt message, writing that not a single day goes by without thinking about, missing, loving and sometimes crying over her friend.
The recent rediscovery of the Oscar de la Renta dress comes during another emotional period for Osbourne. Per People, she also continues to honor her father, Ozzy Osbourne, who passed away in July 2025. Nearly a year after his passing, she paid tribute to the Black Sabbath legend with a tattoo of his signature glasses.
For Osbourne, however, the vintage dress serves as more than a fashion keepsake. It is a reminder of a friendship that continues to hold a special place in her heart.
“Not a day goes by that I don’t miss you #lul.”
