From Madonna’s cone bra to Prince’s avant-garde ensembles, iconic outfits have been making fashion history for centuries. Certain looks become iconic because they’re innovative and push boundaries, or because celebrities wear them in important moments—or both, in some cases. Whatever their origin, iconic outfits and looks stand out in fashion history and are remembered and revered by style-savvy fans around the world. Read on to learn more about the most iconic outfits and looks in the world.

Molly Ringwald’s Pink Puffy Dress in ‘Pretty in Pink’

When Molly Ringwald’s character Andie graced the screen in 1986’s Pretty in Pink, she changed not just the fashion scene of the era, but movie fashion in general. Her signature look—featuring a bright puffy-sleeved dress—is now one of the most iconic movie looks of all time. The dress was created by costume designer Marilyn Vance and is now considered such an iconic look that you can even buy mini- versions of the costume for your favorite dolls.

David Bowie’s Ziggy Stardust Look

David Bowie’s Ziggy Stardust look has become one of the most iconic looks of all time. For his 1972 Aladdin Sane album cover, Bowie put together a one-of-kind ensemble that would go down in history. The look included a red and blue bodysuit decorated with stars and lightning bolts, and iconic red platform boots. The combination of colors and details truly made Bowie stand out and it became a staple part of his stage wardrobe.

Michael Jackson’s Glittery Jacket in the Music Video for “Thriller”

Michael Jackson left his mark on music, dance, and style—part of that mark was left behind by his iconic jacket in the Thriller music video. Jackson’s ensemble featured a long, red, glittery jacket with what is now known as the “zipper of revelation.” Simple, stylish and instantly recognizable, the jacket made Jackson look even more iconic than he already was.

Princess Diana’s “Revenge Dress”

When Princess Diana sparked a small scandal by attending a charity gala one week after her separation from Prince Charles in 1994, her “revenge dress” made a bigger impression than the headlines. The simple navy dress with a plunging neckline, spaghetti straps, and a slit up the front became an iconic look in its own right. Her modern look and bold stance instantly turned the dress into an iconic symbol of style and resilience.

Grace Jones’ Masculine Influenced Look

Grace Jones has made a lasting impression on fashion, music and art with her unique style. Fusing together masculine and feminine elements, she created her own signature look, including silhouette-shaping suits and detailed jumpers. Her clothing was also highly influential in the fashion industry, with designers like Vivienne Westwood, Jean Paul Gaultier, and Issey Miyake drawing inspiration from her style for their own pieces.

Madonna’s Cone Bra

Madonna has been an innovator of style from the very start of her career, often paving the way for fashion trends and shocking audiences with her looks. One of her most iconic outfits was the cone shaped bra designed for her for her Blonde Ambition tour. The cone bra was created by Jean Paul Gaultier, who was inspired by the plastic fashion trend of the early ’90s. It became an instant hit with fans, who proudly wore replica versions of the corset on the streets.

Cher’s Bob Mackie Outfit in the Video for ‘If I Could Turn Back Time’

Cher’s video for her 1989 single, “If I Could Turn Back Time,” was no small feat. The video featured the iconic singer dressed in a Bob Mackie-designed black sequined outfit complete with feathers and a dramatic neckline. This look instantly cemented itself as one of Cher’s most iconic onstage looks, and it showed her fans that she had no limits when it came to fashion and performance.

Prince’s Avant-Garde Ensembles

Prince has been a fashion icon since the ’80s, and his ensembles have pushed the boundaries of style since the very beginning. From the tuxedo he wore to the 1984 American Music Awards (which he accessorized with a custom bow tie) to the bright purple suit and ruffled shirt he wore to the 2015 BET Awards, Prince seamlessly blended together couture, color and structure in his looks.

From Madonna’s cone bra to Cher’s Bob Mackie outfit and Prince’s avant-garde ensembles, these iconic outfits and looks have made an indelible mark on fashion and culture. Whether they were bold, boundary-pushing creations or quietly glamorous ensembles, these pieces will continue to be remembered and revered in the fashion world.