As any good diva knows, when you’ve been in the spotlight for over a decade, you develop a thick rulebook of do’s and don’ts. Mariah Carey has many, the first of which being that she doesn’t celebrate birthdays—rather, “anniversaries.” She also doesn’t do bad lighting, and wears sunglasses most of the time (a pro-tip from model
Christie Brinkley), and the left side of her face is her “good side.” As evidenced in her new docu-series, “ Mariah’s World,” Carey is uber-cautious about cultivating her public image. When it comes to her style, however, she’s much more do than don’t. In the ’90s, she perfected the art of the glamorous yet comfortable going out look, and in the aughts she oscillated between mini skirts and Levi’s. Being a New York native, Carey was the original Carrie Bradshaw, taking the streets in daring crop tops and heels, even while walking her dog. Here, a look back at the iconic singer’s most fabulous fashion moments, from the red carpet to the city sidewalk.
Mariah Carey attends the 33rd Annual Grammy Awards circa 1991 in New York City wearing a little black dress with rhinestone trim and long diamond earrings.
Mariah Carey attends the 19th Annual American Music Awards on January 27, 1992 at the Shrine Auditorium in Los Angeles, California wearing a sequin dress and shimmering tights.
Mariah Carey wears a black slit skirt paired with a black bandeau crop top out in New York City, a look she paired with simple strappy heels.
Mariah Carey was the queen of a good pair of jeans. Here, she sits in the recording studio in a worn pair of Levi’s and a button-up sweater.
Singer Mariah Carey attends the Fall 1994 Fashion Week: Calvin Klein Fashion Show on April 13, 1994 at Bryan Park in New York City in a classic ’90s “Clueless” look.
Singer Mariah Carey attends the 23rd Annual American Music Awards on January 29, 1996 at the Shrine Auditorium in Los Angeles, California wearing leather pants.
Singer Mariah Carey attends the “Seven Years in Tibet” Century City Premiere on October 6, 1997 at the Cineplex Odeon Century Plaza Cinemas in Century City, California.
Singer Mariah Carey attends Sean Combs’ Party to Celebrate the Grand Opening of Justin’s Bar & Restaurant on September 30, 1997 in New York City.
Mariah Carey lets her curly hair down and wears a shimmering gold dress for a night out at the Beacon Theatre in New York City in 1998.
Mariah Carey poses in a pink Chanel houndstooth two-piece with a small dog at a Chanel-hosted lunch at Lincoln Center in New York in 2000.
Karl Lagerfeld poses with Mariah Carey circa 2000. The singer wears a mesh little black dress and the two perfectly match, making us realize they’re actually quite similar.
Mariah Carey wears a sequin butterfly bustier to the ‘VH-1 Divas 2000: A Tribute To Diana Ross’ at Madison Square Garden in New York City.
Mariah Carey wears a pink slip dress to receive her award at the The 6th Annual Blockbuster Awards in the Shrine Auditorium in Los Angeles, California.
Singer Mariah Carey poses for paparazzi photographers July 11, 2001 wearing a “Delicious” tank top as she leaves the Mandarin Oriental Hotel in Knightsbridge, London.
Mariah Carey wears a crochet bustier crop top and a maxi denim skirt to the The 17th Annual Soul Train Music Awards in Los Angeles.
Mariah Carey attends a party to promote her new single “Loverboy” and new album “Glitter” in London wearing a bandana top, denim separates, and a “Glitter” belt.
Mariah Carey poses in a denim mini skirt, “Glitter” tank top, and sunglasses while holding a pink boom box on tour promoting her new album.
Mariah Carey steps out in a pink Juicy Couture velour jumpsuit top, which she paired with jeans, sunglasses, and a rhinestone belt to sign autographs.
Mariah Carey arrives in London wearing a “Honey B. Fly” pink top, denim separates, a diamond chain necklace, and an “Automatic princess” diamond chain belt.
Mariah Carey attended her album launch and birthday party at Tantra in London, Great Britain wearing a fur-trimmed white shawl, a white maxi dress, and lots of jewels.
Mariah Carey steps out to walk her dog in New York City wearing high heels, a yellow bandage dress, and sunglasses. Is this her version of casual?
Singer Mariah Carey throws the ceremonial first pitch before Japanese professional baseball match between Yomiuri Giants and Rakuten Golden Eagles at Tokyo Dome on May 28, 2008 in Tokyo, Japan.
Singer Mariah Carey leaves MTV Studios July 22, 2008 in New York City wearing a rainbow mini skirt and diamond belt and a blue button-up shirt.
Mariah Carey didn’t even let a broken arm get in the way of her glamour. Here she is seen leaving the Ritz-Carlton on July 12, 2013 in New York City with a bedazzled sling.
Mariah Carey didn’t even let a broken arm get in the way of her glamour. Here she is at “The Butler” New York Premiere in a studded sling.