Madonna and Sean Penn’s Wedding

Her hair was in a classic French twist and covered with a black bowler draped in cream-colored tulle. Though at the time she was known for wearing a stack of bangles on her arms and giant crucifix necklaces, for jewelry, she opted for a single long earring and an antique pearl bracelet.

Draped across her dress like a beauty contestant’s sash was a silver-and-pink silk metallic net, dripping with encrusted jewels, pearls and dried roses. “We wanted a ’50s feeling,” designer Stewart would say later, “something Grace Kelly might have worn.” Madonna walked down the aisle on the arm of her father to the song “Moments of Love.” Actor James Foley was Penn’s best man, while Madonna’s sister Paula was the maid of honor.

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