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red carpet derby
May 7, 2018

The Biggest Fashion Misses of the Met Gala Over the Years

By Véronique Hyland

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Photo: Getty Images

Victoria Beckham, Sarah Jessica Parker, and Freida Pinto: three women who may rule the best-dressed lists now, but whose previous Met Gala looks include some moments they’d probably rather forget. (And designers and fashion editors didn’t fare much better.)
As we gird our loins for the Catholicism-themed Met Gala — dress code “Sunday best” — here’s a look at some of the most questionable moments from the annual event over the years. Warning: High-fashion bunny ears, bullfighter costumes, flaming headdresses, and some confusing midriff-baring lie ahead.

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1 / 18 Photos
Jessica Simpson, 2001.

Simpson was early to the Unicorn-frappuccino color scheme.

Photo: Evan Agostini/Getty Images
Jamie-Lynn Sigler, 2003.

An important thing to note about this gown adaptation of the aughts-beloved T-shirt style is that it was worn to the "God...

Jamie-Lynn Sigler, 2003.

An important thing to note about this gown adaptation of the aughts-beloved T-shirt style is that it was worn to the "Goddess"-themed gala.

Zac Posen and Stella Schnabel, 2004.

In which Posen fights bulls not with a red flag but with the power of his moody gaze.

Photo: Dimitrios Kambo...
Zac Posen and Stella Schnabel, 2004.

In which Posen fights bulls not with a red flag but with the power of his moody gaze.

Photo: Dimitrios Kambouris/WireImage
3LW, 2001.

Imagine being invited to the Met Gala and wearing this.

Photo: Evan Agostini/Getty Images
Victoria Beckham, with Stefano Gabbana and Domenico Dolce, 2003.

Beckham probably wants to forget this look from her pre-fashion-designer days.

Jennifer Love Hewitt, 1999.

Hewitt's interpretation of the "Rock Style" theme? A bare midriff and feathered white skirt.

Photo: Mari Sarai/G...
Jennifer Love Hewitt, 1999.

Hewitt's interpretation of the "Rock Style" theme? A bare midriff and feathered white skirt.

Photo: Mari Sarai/Getty Images
Anna Wintour, 2004.

Just because you host fashion's biggest night out doesn't mean you always get it right.

Polly Mellen, 1989.

A corollary: Just because you're a legendary fashion editor doesn't mean you always get it right.

Photo: Ron Galella/WireImage
Hillary Clinton, 2001.

This one does not win the popular vote.

Photo: George De Sota/Getty Images
Sandra Lee, 2014.

This Franken-bridal look — complete with elbow-length gloves — might go down in history as the worst look in the history of the ...

Sandra Lee, 2014.

This Franken-bridal look — complete with elbow-length gloves — might go down in history as the worst look in the history of the event.

Photo: Dimitrios Kambouris/Getty Images
Madonna, 2009.

Even Madonna struggles to pull off $350 Louis Vuitton bunny ears.

Photo: Patrick McMullan/Patrick McMullan via Getty Image
Freida Pinto, 2011.

When Gordon Gekko boardroom-wear met formalwear.

Photo: Stephen Lovekin/Getty Images
Kimora Lee Simmons, 2008.

Simmons's stained-glass gown is lacking in her usual fabulosity.

Photo: Stephen Lovekin/Getty Images
Sarah Jessica Parker, 2015.

The headdress that launched a thousand memes.

Photo: Larry Busacca/Getty Images
John Galliano, 2001.

Taking into account his over-the-top ensembles for his runway bows, this floral suit is comparatively tame.

Photo: George De Sota...
John Galliano, 2001.

Taking into account his over-the-top ensembles for his runway bows, this floral suit is comparatively tame.

Photo: George De Sota/Getty Images
Jessica Simpson and John Mayer, 2007.

While Jessica Simpson probably regrets this elephant-trainer ensemble, we're guessing she regrets bringing John M...

Jessica Simpson and John Mayer, 2007.

While Jessica Simpson probably regrets this elephant-trainer ensemble, we're guessing she regrets bringing John Mayer even more.

Photo: Evan Agostini/Getty Images
Serena Williams, 2011.

When fascinators reached saturation point, Williams was there to officially bury the trend with this topper.

Photo: Stephen Lov...
Serena Williams, 2011.

When fascinators reached saturation point, Williams was there to officially bury the trend with this topper.

Photo: Stephen Lovekin/Getty Images
Nicki Minaj, 2017.

Sorry, but strapping Kawakubo's face to a bodysuit does not a tribute make

Photo: Neilson Barnard/Getty Images
1 / 18

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