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Happy Birthday, Madonna! 5 of Her Best Music Video Looks Ever—And How to Get Them

Photo: Getty Images

Photo: Getty Images

It’s hard to believe Madonna is turning 57 today, especially when you watch her music videos. (There are 68 total, if you’ve got that kind of time.) While the headbands and permed bangs should probably remain in our collective memories, the music, dancing, and outfits are just as great today as they were when they first hit MTV. Whether Madge was belting it out in a gender-bending suit in 1989’s “Express Yourself” or wearing what is arguably the modern girl’s uniform—high-rise jeans, a striped tee, and leather jacket—in 1986’s “Papa Don’t Preach,” clothes were no doubt a huge part of her story. Below, we picked five of Madonna’s most stylish videos ever, plus tips for getting each look.

“Open Your Heart,” 1986

Madonna’s music videos often played out like mini movies, complete with complex themes and characters. In “Open Your Heart,”she explored voyeurism and sexuality as an exotic dancer who escapes a seedy strip club. Her androgynous look—consisting of a cropped gray blazer, brogues, and a trilby hat—became an early signature.

Photos: Courtesy of StyleBop; Courtesy of Net-a-Porter; Courtesy of Barneys New York

Photos: Courtesy of StyleBop; Courtesy of Net-a-Porter; Courtesy of Barneys New York

The Kooples blazer
US $545; AED/SAR 2,000
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Maison Michel hat
US $440; AED/SAR 1,616
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Gianvito Rossi shoes
US $790; AED/SAR 2,900
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“Like a Prayer,” 1989

Slip dresses are everywhere right now, but you won’t find one quite like Madonna’s in “Like a Prayer.”She accessorized hers with a cross necklace and lacy bra, which likely didn’t help her case when the Vatican condemned the video.

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Photos: Courtesy of The Dreslyn; Courtesy of Farfetch; Courtesy of 1stdibs

Organic by John Patrick dress
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Fleur du Mal bra
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Vintage necklace
US $495; AED/SAR 1,818
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“Papa Don’t Preach,” 1986

Madonna’s gamine haircut got all the attention when this video debuted, but her outfit in “Papa Don’t Preach” had real staying power: High-rise jeans, a striped T-shirt, and a leather jacket are all we want to wear these days.

Photos: Courtesy of Laer; Courtesy of Matches Fashion; Courtesy of Net-a-Porter

Photos: Courtesy of Laer; Courtesy of Matches Fashion; Courtesy of Net-a-Porter

Laer jacket
US $775; AED/SAR 2,847
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MiH Jeans jeans
US $265; AED/SAR 973
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T by Alexander Wang top
US $140; AED/SAR 514
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“Vogue,” 1990

Madonna introduced vogueing to the masses in a mix of twenties- and thirties-era outfits, including a lace bodysuit and matching silver cuffs. We can picture starlets wearing something similar today with cigarette pants or a high-rise skirt.

Photos: Courtesy of Journelle; Courtesy of Dylanlex; Courtesy of Birchbox

Photos: Courtesy of Journelle; Courtesy of Dylanlex; Courtesy of Birchbox

La Perla bodysuit
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Dylanlex cuff
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R+Co Sunset Blvd Blonde Shampoo,
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“Express Yourself,” 1989

In “Express Yourself,” which was, at the time, the most expensive music video ever produced, Madonna played with gender roles again and channeled a high-powered businessman. Wear a similar double-breasted suit, looking-glass necklace, and slicked-back hair today with chic pumps and minimal makeup.

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Photos: Courtesy of Net-a-Porter (2); Courtesy of Tradesy

Versace blazer
US $2,750; AED/SAR 10,101
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Versace pants
US $1,325; AED/SAR 4,867
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Chanel necklace,
US $1,338; AED/SAR 4,915
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—Emily Farra, Style.com

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