9 of Amy Winehouse's most iconic looks

Winehouse's stylist and friend Naomi Parry said that the "Back to Black" singer never shied away from expressing her individuality through fashion.

"Amy dressed how she wanted to dress," Parry told uDiscover Music. "No one ever told her."

Winehouse, who won the best female solo artist award at the 2004 Brit Awards, layered the scarlet satin Karen Millen dress over a black lace bra and accessorized with a black leather clutch.

Her styling choice proved Winehouse was decades ahead of her time, as the exposed-bra look was one of the hottest red-carpet trends in 2023.

The dress later sold at an auction for $31,250.

Winehouse began rocking her trademark exaggerated beehive hairstyle in 2007, following the music video for "Back to Black."

Her hairstylist, Alex Foden, later revealed that the heavily backcombed hairstyle initially started as "a joke" on the music video set, Metro UK reported.

"As a joke, I backcombed her hair massively and put an extra packet of hair in," Foden said. "I said, 'There you go, let's go and show the finished look,' taking the piss obviously, and as we came out the trailer, everybody went, 'Oh my God! That is it, that is the signature look.'"

Winehouse was never afraid to experiment with bold colors and playful accessories. She paired the yellow minidress from Preen with red satin heels, a matching nail color, red polka-dot hoop earrings, and a heart-shaped purse — a subtle nod to the awards taking place on Valentine's Day.

Her stylist, Parry, later told Grazia that the singer was such a fan of the dress and "just felt amazing" on the night that she bought half of the collection afterward.

Casual, yet memorable — the simple ensemble that Winehouse wore when she graced the stage at Coachella in 2007 consisted of blue jean shorts, a rust-colored belt, patterned heels, and a tank top exposing colorful bra straps.

The outfit was likely one of Winehouse's favorites, as she wore an identical look to the Isle of White festival in the UK months later.

Winehouse wore a deep-blue minidress adorned with floral appliqué. Staying true to her individuality, she accessorized her beehive with three colorful drink umbrellas.

The dress may be one of the most recognizable from her music career, but the performance she wore it for became memorable for the wrong reasons.

During her set, Winehouse was filmed getting into a physical altercation with a fan, who later said the incident was a case of mistaken identity.

"I saw a hat being thrown from behind me, and it hit Amy's beehive," the fan told the BBC, according to NME. "She looked down, saw me looking up, and her elbow went for me."

"At the end of the day, it is all part of being at the front and being pushed by thousands of people," the fan added. "It is all part of the Glastonbury experience. I'm just pleased I got to see her. She did a great act."

Winehouse wore red denim shorts with a classic early 2000s chunky belt. She paired it with a black tank top under a cropped leather jacket.

The look was yet another example of Winehouse's love of retro-inspired clothing pieces and how she was able to make them edgy enough for the era.

Winehouse, who joined her friend and producer Mark Ronson onstage for the surprise performance, paired the low-cut tank top and white lace bra with jeans and heels.

As with nearly every performance where she wore her beehive hairstyle, she accessorized with a colorful hairpiece.

The green-and-black striped minidress featured a halterneck neckline and was designed by Winehouse's close friend and stylist, Parry.

It would be the last iconic minidress Winehouse wore onstage. A month after performing at the 2011 Summer Festival Tour in Belgrade, Serbia, she died from accidental alcohol poisoning on July 23, 2011.

In 2021, the dress sold at an auction for $243,200. The proceeds went to the Amy Winehouse Foundation, a charity organization founded by her family that supports vulnerable young adults and raises awareness about substance addiction.