Craziest Shoes at the Grammys

Madonna wore red platform boots with a Gaultier look while she performed at the 1999 Grammy Awards.
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Every year, the Grammys celebrate achievements in the music industry — in addition to gold gramophone-shaped trophies being handed out, the star-studded event can be counted on to deliver an array of stylish looks. The red carpet and concert stage present an opportunity for musicians to show off their fashion sense, and that sometimes means showcasing a bold or unconventional shoe. Back in 1999, for example, Madonna gave a performance to remember in a striking pair of platform scarlet red boots.
Erykah Badu made a statement on the red carpet in 2002 wearing super chunky platform boots that looked fit for an excursion in space. In 2016, Lady Gaga turned heads in a red pair of gravity-defying platform pumps with sky-high stiletto heels, a custom pair from Stuart Weitzman that accompanied one of her outfits paying tribute to the late David Bowie. In 2024, Miley Cyrus displayed a creative design with a Tabi shoe hailing from a collaboration between Maison Margiela and Christian Louboutin. See below for these looks and more striking shoes worn at the Grammys over the years.
Madonna wore red platform boots with a Gaultier look while she performed at the 1999 Grammy Awards.
Wearing chunky platform boots, Erykah Badu attends the 44th Annual Grammy Awards on February 27, 2002 in Los Angeles, CA.
Lady Gaga wears a Marc Jacobs coat dress with sky-high heels at the 2016 Grammy Awards.
A closer look at Lady Gaga’s footwear.
Dencia wears a pink jumpsuit with embellished platform heels at the 2016 Grammy Awards.
Nadeea Volianova wears a teal dress with knee-high boots at the Grammys in 2014.
Robyn wears platform Timberlands at the 2012 Grammys.
Ciara wears cool ankle-strap sandals at the Grammys in 2011.
Lady Gaga at the 2010 Grammy Awards.
Pink wears a sheer black dress with black gladiator boots at the 2003 Grammy Awards.
Sheryl Crow wears a romper with matching cowboy boots at the 2002 Grammys.
Shelby Lynne in shiny baby blue boots at the Grammy Awards in 2001.
Wearing sandals with heels in the shape of her initials ‘M’ and ‘C,’ Miley Cyrus attends the 61st Annual GRAMMY Awards at Staples Center on February 10, 2019 in Los Angeles, California.
Wearing a pair of chunky black boots, Billie Eilish attends the 64th annual Grammy Awards at the MGM Grand Garden Arena in Las Vegas on April 3, 2022.
Miley Cyrus at the 66th Annual GRAMMY Awards held at Crypto.com Arena on February 4, 2024 in Los Angeles, California.
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