Cyndi Lauper’s Most Iconic Fashion Moments Through the Years

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Cyndi Lauper has been a fashion icon since she burst onto the music scene in the early 1980s. Her bold, eclectic style has influenced countless fans and fashionistas over the decades. Here are some of her most iconic fashion moments:

1. “Girls Just Want to Have Fun” Music Video (1983)

Lauper’s breakout hit also introduced her distinctive style to the world. In the music video, she sported a colorful, mismatched outfit featuring a red off-the-shoulder top, a ruffled skirt, and vibrant accessories. Her wild, multi-colored hair and eclectic mix of patterns and textures became her signature look.

2. Grammy Awards (1984)

At the 1984 Grammy Awards, where she won Best New Artist, Lauper wore a bright red dress with a voluminous skirt and a tight, sequined bodice. Her hair was styled in her trademark colorful, messy look, and she accessorized with chunky jewelry, setting her apart from the more conservative styles of the evening.

3. “We Are the World” Recording (1985)

During the recording of the iconic charity single “We Are the World,” Lauper wore a distinctive outfit that included a headscarf, oversized sunglasses, and a colorful jacket adorned with pins and patches. Her quirky accessories and layered look embodied her playful and rebellious fashion sense.

4. “True Colors” Album Cover (1986)

For the cover of her second studio album, “True Colors,” Lauper embraced a softer, yet equally striking look. She wore a flowing, rainbow-hued dress that complemented the album’s theme. Her hair, though still colorful, was styled in softer waves, showing a more ethereal side of her fashion sense.

5. VH1 Fashion and Music Awards (1995)

At the 1995 VH1 Fashion and Music Awards, Lauper wore a dramatic, avant-garde ensemble featuring a metallic, futuristic dress with a high collar and exaggerated shoulders. Her hair was styled in a sleek, platinum blonde bob, proving that her fashion sense was as cutting-edge as ever.

6. Tony Awards (2013)

When Lauper attended the Tony Awards in 2013, where she won for Best Original Score for the musical “Kinky Boots,” she wore a stunning, floor-length black gown with intricate lace details. Her look was elegant yet still distinctly her own, complete with bold makeup and her signature bright red hair.

7. Met Gala (2019)

At the 2019 Met Gala, themed “Camp: Notes on Fashion,” Lauper wowed with a dazzling, punk-inspired ensemble. She wore a metallic, silver suit with exaggerated shoulders and a deep V-neck, accessorized with bold jewelry and her hair styled in a high, platinum blonde pompadour. The look perfectly encapsulated the theme and showcased her enduring ability to surprise and inspire with her fashion choices.

8. Cyndi Lauper & Friends: Home for the Holidays Concert (2020)

In her annual holiday benefit concert, Lauper often dons festive and flamboyant outfits. In 2020, she wore a bright, multi-colored suit with glittery accents and her signature bold makeup. Her look was both festive and quintessentially Cyndi, embodying her vibrant personality and commitment to using fashion as a form of self-expression.

Cyndi Lauper’s fashion journey is a testament to her creativity and individuality. She has consistently pushed boundaries and embraced a wide range of styles, from punk and new wave to glamorous and avant-garde. Her fearless approach to fashion continues to inspire and influence the industry.


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