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.
The Kooples blazer
US $545; AED/SAR 2,000
Buy it now
Maison Michel hat
US $440; AED/SAR 1,616
Buy it now
Gianvito Rossi shoes
US $790; AED/SAR 2,900
Buy it now
“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.
Organic by John Patrick dress
US $190; AED/SAR 698
Buy it now
Fleur du Mal bra
US $160; AED/SAR 588
Buy it now
Vintage necklace
US $495; AED/SAR 1,818
Buy it now
“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.
Laer jacket
US $775; AED/SAR 2,847
Buy it now
MiH Jeans jeans
US $265; AED/SAR 973
Buy it now
T by Alexander Wang top
US $140; AED/SAR 514
Buy it now
“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.
La Perla bodysuit
US $1,414; AED/SAR 5,194
Buy it now
Dylanlex cuff
US $290; AED/SAR 1,065
Buy it now
R+Co Sunset Blvd Blonde Shampoo,
US $29; AED/SAR 107
Buy it now
“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.
Versace blazer
US $2,750; AED/SAR 10,101
Buy it now
Versace pants
US $1,325; AED/SAR 4,867
Buy it now
Chanel necklace,
US $1,338; AED/SAR 4,915
Buy it now
—Emily Farra, Style.com