Grammy's All Time Fashion Hits & Misses

From Gwen's haute couture to Queen Latifah's faux pas, check out the best and worst fashions from recent Grammy Awards. By Serena Kappes

01 of 14

GWEN STEFANI: HIT

GWEN STEFANI: HIT
Kevin Mazur/WireImage

Stefani – who was up for best female pop vocal performance for "What You Waiting For?" – was anything but basic in a sheer black Viktor amp Rolf minidress in 2005.

02 of 14

QUEEN LATIFAH: MISS

QUEEN LATIFAH: SLAM
Mark J. Terrill/AP

A dress? Pants? In 2004, the rapper-singer-actress just couldn't make up her mind – and didn't flatter her trimmed-down figure.

03 of 14

BRITNEY SPEARS: HIT

BRITNEY SPEARS: HIT
Jerzy Dabrowsky/ZUMA

Though she lost to Christina Aguilera as best new artist in 2000, the pop diva reigned supreme in an elegant Randolph Duke gown and Oscar de la Renta mink stole.

04 of 14

AVRIL LAVIGNE: MISS

HOW AWFUL
Kevin Mazur/WireImage.com

She should have stuck with her day job: In 2003, the best new artist nominee looked more like a "Sk8ter Boi" in her message-scrawled tuxedo jacket, which she helped design.

05 of 14

USHER: HIT

USHER: HIT
Robert Galbraith/REUTERS/Landov

The RampB singer (who scored three awards) lit up the red carpet in 2005 in a dapper white Armani ensemble, wingtip shoes and plenty of bling.

06 of 14

CHRISTINA AGUILERA: MISS

CHRISTINA AGUILERA: MISS
Frank Foden/ZUMA

"This dress weighs more than I do," the best new artist winner complained about her chain-mail dress in 2000. Sadly, the tacky frock wasn't worth the weight.

07 of 14

BEYONCé: HIT

BEYONCé: BEST
REUTERS/Robert Galbraith/Landov

Bootylicious, indeed. The singer (nominated with Destiny's Child for "Lose My Breath") flaunted her curves last year in a Roberto Cavalli gown she called "simple and sexy."

08 of 14

SHERYL CROW: MISS

SHERYL CROW: WORST
REUTERS/Robert Galbraith/Landov

In 2005, Crow (nominated for "The First Cut Is the Deepest") joked that her unflattering cutout halter dress was made from then-boyfriend Lance Armstrong's old Tour de France jerseys.

09 of 14

ALICIA KEYS & ASHANTI: HIT

ALICIA KEYS & ASHANTI: HIT
Robyn BECK/AFP/Getty; Mark J. Terrill/AP

In 2004, Keys wore a flowing peaches-and-cream Roberto Cavalli bustier with capris, while double-nominee Ashanti worked a variation on the theme in a crisscross Cavalli gown.

10 of 14

JOHN MAYER: MISS

JOHN MAYER: WORST
Lester Cohen/WireImage.com

Call him Sgt. Pepper: In 2005, John Mayer (who won two Grammys for his song "Daughters") played dress-up, badly, in a Beatles-inspired velvet blazer.

11 of 14

MARY J. BLIGE: MISS

MARY J. BLIGE: MISS
Gregg DeGuire/WireImage

The big-voiced RampB diva (a 2004 winner for her duet with Sting, "Whenever I Say Your Name") looked more like Big Bird in her bright yellow ensemble.

12 of 14

MADONNA: HIT

MADONNA: GLAM
Kevork Djansezian/AP

To introduce Sting and best new artist nominee Sean Paul in 2004, Madge opted for a subtle Versace wrap dress that proved she didn't have to shock to make a splash.

13 of 14

LIL' KIM: MISS

LIL' KIM: SLAM
Mark J. Terrill/AP

The diminutive hip-hopper (a multiple nominee in 2004) left little to the imagination in a revealing fur-collared gown.

14 of 14

SHAKIRA: MISS

GOLDEN GIRL
Steve Granitz/WireImage

"I wanted to be in gold tonight," Shakira told PEOPLE about her blinding metallic get-up in 2001. But all the gold she really needed was her trophy for best Latin pop album.

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