The Met Gala is where celebrities ascend to style icon status. On the first Monday in May, stars don’t just walk the red carpet, they climb the steps of the Metropolitan Museum in statement couture presenting their interpretation of the exhibition’s theme to the entire world. Unlike an awards show or a premiere, the goal isn’t to shine for a moment, it’s to create a look that resonates for decades. Despite the wealth of designer gowns and bespoke suits, few accomplish that feat, but those who do earn themselves a place in fashion history. The greatest hits—Rihanna’s papal chic, Kate Moss’s golden turban, Sarah Jessica Parker’s tartan Alexander McQueen, Erykah Badu’s glittering top hat, Madonna in a hippie caftan—rank among the best outfits ever to be worn. And their charms wouldn’t have been as compelling on another night.
The gala encourages the kind of innovation rarely seen elsewhere. The Costume Institute’s trove of landmark runway creations serves as an inspiration for guests, allowing them to take on fashion at its most avant-garde. Where else will you see Cardi B. and a small army of assistants move a mountainous red Thom Browne train across a pink carpet? Or watch awestruck as Lady Gaga and Brandon Maxwell take their magenta nesting doll ballgown to the streets, much to the delight of New Yorkers. A standout Met look can be performative (Amber Valletta going full baroque in 2004), subversive (Daphne Guinness in a plume of McQueen feathers in 2011), witty (Karolina Kurkova’s playful Viktor and Rolf in 2015, or referential (the Olsen twins and their yearly vintage surprise), it just can’t be boring.
The celebration in honour of the “About Time” show was cancelled due to the COVID-19 crisis, but fashion’s biggest night returns this year with a fete in honour of America: A Lexicon of Fashion. A look back on the event’s best and boldest outfits represents fashion at its most inspiring. Here, see the most memorable, daring, and over the top outfits ever.

1 / 117
Kate Moss in Calvin Klein, 1995

2 / 117
Naomi Campbell in Versace, 1995

3 / 117
Madonna in Versace, 1997

4 / 117
Elizabeth Hurley in Versace, 1997

5 / 117
Sean Combs and Jennifer Lopez, 1999

6 / 117
Amber Valetta in Versace, 1999

7 / 117
Liv Tyler in Stella McCartney, 1999

8 / 117
Gwyneth Paltrow in Gucci, 1999

9 / 117
Lil' Kim in Versace, 1999

10 / 117
Whitney Houston, 1999

11 / 117
Demi Moore in Donna Karan, 2000

12 / 117
Hillary Clinton in Oscar de la Renta, 2000

13 / 117
Lee Radziwill in Armani, 2000

14 / 117
Christy Turlington in Saint Laurent, 2001

15 / 117
Stephanie Seymour in Alaia, 2001

16 / 117
Marie-Chantal Miller in Valentino Couture, 2001

17 / 117
Carmen Kass in Gucci, 2003

18 / 117
Davie Bowie and Iman in Calvin Klein, 2003

19 / 117
Diana Ross in Tom Ford, 2003

20 / 117
Nicole Kidman in Tom Ford, 2003

21 / 117
Amber Valleta in a Maggie Norris Couture Corset, John Galliano Skirt, 2004

22 / 117
Linda Evangelista in Jean Paul Gaultier Couture, 2004

23 / 117
Scarlett Johansson in Calvin-Klein, 2004

24 / 117
Karolina Kurkova in Viktor and Rolf, 2005

25 / 117
Vanessa Paradis in Chanel, 2005

26 / 117
Charlize Theron in Christian Dior, 2006

27 / 117
Charlotte Gainsbourg in Balenciaga, 2006

28 / 117
Sarah Jessica Parker in Alexander McQueen, 2006

29 / 117
Sienna Miller in Burberry, 2006

30 / 117
Cameron Diaz in Christian Dior, 2007

31 / 117
Cate Blanchett in Balenciaga, 2007

32 / 117
Charlotte Gainsbourg in Balenciaga, 2007

33 / 117
Daria Werbowy in Azzedine Alaia, 2007

34 / 117
Jennifer Connelly in Balenciaga, 2007

35 / 117
Renee Zellweger in Carolina Herrera, 2007

36 / 117
Shalom Harlow in Viktor and Rolf, 2007

37 / 117
Christina Ricci in Givenchy, 2008

38 / 117
Gisele Bundchen in Versace, 2008

39 / 117
Julia Roberts in Armani, 2008

40 / 117
Kate Moss in Marc Jacobs, 2009

41 / 117
Madonna in Louis Vuitton, 2009

42 / 117
Miranda Kerr in Jil Sander, 2009

43 / 117
Gwen Stefani, 2010

44 / 117
Doutzen Kroes in Zac Posen, 2010

45 / 117
Oprah in Oscar de la Renta, 2010

46 / 117
Beyonce in Emilio Pucci, 2011

47 / 117
Daphne Guinness in Alexander McQueen, 2011

48 / 117
Daphne Guinness in Alexander McQueen, 2011

49 / 117
Liv Tyler in Givenchy, 2011

50 / 117
Madonna in Stella McCartney, 2011

51 / 117
Michelle Williams in Miu Miu, 2011

52 / 117
Naomi Campbell in Alexander McQueen, 2011

53 / 117
Anja Rubik in Antony Vaccarello, 2012

54 / 117
Carey Mulligan in Prada, 2012

55 / 117
Rooney Mara in Givenchy, 2012

56 / 117
Scarlett Johansson in Dolce & Gabbana, 2012

57 / 117
Stella Tennant in Christopher Kane, 2013

58 / 117
Ashley Olsen in Dior, 2013

59 / 117
Kim Kardashian in Givenchy, 2013

60 / 117
Sarah Jessica Parker in Phillip Treacy and Giles Deacon, 2013

61 / 117
Dita von Tesse in Zac Posen, 2014

62 / 117
David Beckham in Ralph Lauren Black Label and Victoria Beckham in Victoria Beckham, 2014

63 / 117
Erykah Badu in Givenchy, 2014

64 / 117
Lupita Nyongo in Prada, 2014

65 / 117
Monica Belluci in Dolce and Gabbana, 2014

66 / 117
Rihanna in Guo Pei, 2015

67 / 117
Alexa Chung in Erdem, 2015

68 / 117
Anne Hathaway in Ralph Lauren, 2015

69 / 117
Chloe Sevigny in J.W. Anderson, 2015

70 / 117
Grace Coddington in Michael Kors, 2015

71 / 117
FKA Twigs in Christopher Kane, 2015

72 / 117
Sienna Miller in Thakoon, 2015

73 / 117
Lady Gaga in Alexander Wang, 2015

74 / 117
Miley Cyrus in Alexander Wang, 2015

75 / 117
Solange in Giles Deacon, 2015

76 / 117
Blake Lively in Burberry, 2016

77 / 117
Florence Welch in Gucci, 2016

78 / 117
Beyonce in Givenchy, 2016

79 / 117
Brie Larson in Proenza Schouler, 2016

80 / 117
Emma Watson in Jean Paul Gaultier, 2016

81 / 117
Gigi Hadid in Tommy Hilfiger, 2016

82 / 117
Lena Dunham, Jenni Konner, and Jenna Lyons in Creatures of the Wind, 2016

83 / 117
Lupita Nyongo in Calvin Klein, 2016

84 / 117
Poppy Delevingne in Marchesa, 2016

85 / 117
Selena Gomez in Louis Vuitton, 2016

86 / 117
Taylor Swift in Louis Vuitton, 2016

87 / 117
Bella Hadid in Alexander Wang, 2017

88 / 117
Caroline Kennedy in Comme des Garçons, 2017

89 / 117
Jennifer Lopez in Valentino, 2017

90 / 117
Julie Macklowe in Comme des Garçons, 2017

91 / 117
Katy Perry in Maison Margiela Artisanal designed by John Galliano, 2017

92 / 117
Kendall Jenner in La Perla, 2017

93 / 117
Kylie Jenner in Versace, 2017

94 / 117
Lily Rose Depp in Chanel, 2017

95 / 117
Michelle Lamy in Comme des Garçons, 2017

96 / 117
Rihanna in Comme des Garçons, 2017

97 / 117
Zendaya in Dolce & Gabbana, 2017

98 / 117
Amal Clooney in Richard Quinn, 2018

99 / 117
Frances McDormand in Valentino, 2018

100 / 117
Karen Elson in Dolce and Gabbana, 2018

101 / 117
Kim Kardashian in Versace, 2018

102 / 117
Lena Waithe in Carolina Herrera, 2018

103 / 117
Rihanna in Maison Margiela Artisanal designed by John Galliano, 2018

104 / 117
Zendaya in Jean Paul Gaultier, 2018

105 / 117
Katy Perry in Moschino, 2019

106 / 117
Katy Perry in Moschino, 2019

107 / 117
Jared Leto in Gucci

108 / 117
Cardi B in Thom Browne, 2019

109 / 117
Billy Porter in The Blondes, 2019
This article was originally published on Vogue.com.

110 / 117
Kristen Stewart in Chanel, 2021

111 / 117
Lorde in Bode, 2021

112 / 117
Grimes in Iris van Herpen, 2021

113 / 117
Isabelle Huppert in Balenciaga, 2021

114 / 117
Iman in Dolce&Gabbana x Harris Reed, 2021

115 / 117
Timothée Chalamet in Haider Ackermann, 2021

116 / 117
Kendall Jenner in Givenchy, 2021

117 / 117