When Madonna and Sean Penn traded vows beneath a white tent perched in Malibu, Calif., on Aug. 16, 1985, their guest list ...

From her “Like a Virgin” wedding dress to her boundary-pushing street style, Madonna’s fashion choices have always been daring and influential.

Nothing says "painfully '80s" like our favorite celebrities and their fashion choices of decades past. From the brightly ...

"Mom, I am a rich man."From there, Madonna continued to flaunt her singular fashion sense with an emphasis on boudoir style. She doubled up on lingerie dresses in another look, wearing a lace slip ...

Paging pop royalty! When it comes to epic dance bops, Madonna and Britney Spears are the undisputed queen and princess of pop. Over the years, the two iconic singers have even collaborated to give us ...

Britney rival Aguilera (No. 6 on the list), the young singer who never leaves the house with her navel covered, could also use some fashion help, while pop weirdo and actress Bj ö rk (No. 3), who ...

Madonna is hoping to go from fashion icon to fashion mogul with her latest endeavor. The pop star and her 13-year-old daughter, Lourdes Maria Ciccone Leon, are partnering on a ...