-
Katie Holmes: 1998
Katie Holmes in a white dress and sandals on the red carpet at the 1998 Emmy Awards in Los Angeles. She became a late ’90s icon from her role on “Dawson’s Creek” (1998-2003).
-
Katie Holmes: 2019
Katie Holmes wears Saint Laurent at the Nordstrom NYC Flagship store opening party on Oct. 22, 2019. In 2019, there is renewed interest around Holmes’ style.
-
Céline Dion: 1999
Céline Dion at the 1999 Grammy Awards. In the ’90s, she had a number of hits, such as “My Heart Will Go On” from the film “Titanic.”
-
Céline Dion: 2019
Céline Dion wears a Max Mara fall ’19 outfit in New York in November 2019. After mourning the loss of husband René Angélil in 2016, Dion began working with celebrity stylist Law Roach. She now is known for her haute couture looks.
-
Shania Twain: 1999
Shania Twain performs “Man, I Feel Like a Woman,” during the 41st annual Grammy Awards in 1999. In 2003, Twain fell ill with dysphonia, a vocal cord muscle paralysis caused by Lyme disease, and was forced to retire from music.
-
Shania Twain: 2019
Shania Twain in Dolce & Gabbana in 2019 at an event in Las Vegas. After undergoing an operation to correct her vocal cords, Twain has returned to music, with a residency in Vegas through March 2020.
-
Tia and Tamera Mowry: 1996
Tia (L) and Tamera Mowry at the 27th Annual Naacp Image Awards in 1996. Their Disney Channel show, “Sister, Sister” aired from 1994 through 1999.
-
Tia and Tamera Mowry: 2019
Tia (L) and Tamera Mowry in 2019. Tia is pictured at the “It’s a Wonderful Lifetime” celebration in October; Tamera is pictured at the People’s Choice Awards in November. Tia appears on the Netflix show “Family Reunion,” while Tamera is a talk show host on “The Real.”
-
Natasha Lyonne: 1999
Natasha Lyonne wears an all-black look to a 1999 Motorola party. In the ’90s, Lyonne was famous for roles in “American Pie” and “But I’m a Cheerleader,” but she was plagued in the early ’00s by substance abuse issues.
-
Natasha Lyonne: 2019
Natasha Lyonne in Rodarte at the 2019 InStyle Awards. From 2013-2019, she starred as Nicky Nichols on “Orange Is the New Black,” revamping her career. This year, she earned huge buzz for writing and acting on Netflix’ “Russian Doll.”
-
Missy Elliott: 1997
Missy Elliott wearing an all-white look complete with sneakers at a charity gala in New York in 1997. In the ’90s and early ’00s, Elliott was one of the biggest female rappers in the game.
-
Missy Elliott: 2019
Missy Elliott at the 2019 Video Music Awrds, where she won the MTV Michael Jackson Vanguard Award. Elliott took a break from the music space in the 2000s due to a Graves’ disease diagnosis but dropped her first EP since 2005, “Iconology,” in August.
-
Martha Stewart: 1997
Martha Stewart arrives to a Marc Jacobs show at New York Fashion Week in 1997. Stewart became known for her cookbooks in the 1990s but fell out of the spotlight in the early 2000s, when she was sentenced to jail for insider trading.
-
Martha Stewart: 2019
Martha Stewart wearing a silk yellow look with sandals at the Time 100 Gala in April 2019. Since being released from prison in 2005, the star has written more cookbooks, appeared on television programs and launched a shoe line with Aerosoles.
-
Winona Ryder: 1999
Winona Ryder in an all-black look at the “Girl, Interrupted” premiere in 1999. Ryder was a huge star of the ’90s — with two Oscar nominations — but fell out of the spotlight after a 2001 arrest for shoplifting.
-
Winona Ryder: 2019
Winona Ryder in an all-black look at the “Stranger Things” season premiere in June 2019. The Netflix show has been part of the star’s comeback, earning her a Screen Actors Guild Award in 2016.
-
Regina King: 1999
Regina King in a white dress and square-toe sandals at the 1999 Academy Awards. King rose to fame in the ’80s as Brenda Jenkins on “227” and strung together a series of film roles in the ’90s.
-
Regina King: 2019
Regina King wearing a white strapless Oscar de la Renta gown gown with matching Louboutin Pigalle Follies at the 2019 Academy Awards, where she won Best Supporting Actress for “If Beale Street Could Talk.” In addition to her Oscars win this decade, King arguably landed the biggest role of her career on “American Crime,” earning two Emmy Awards for the role.
-
Robin Wright: 1999
Robin Wright pictured with then-husband Sean Penn at the 1999 premiere of “Message in a Bottle.” Wright rose to fame in 1987 with “Princess Bride” and starred in 1994’s hit “Forrest Gump.”
-
Robin Wright: 2019
Robin Wright wears strappy sandals with a plunging gown at the 2019 SAG Awards. After having few major roles in the ’00s, Wright re-rose to prominence with the lead role in Netflix’s “House of Cards” (2013-2017).
-
Jodei Sweetin: 1993
Jodie Sweetin in 1993. In the ’90s, Sweetin was famous for starring as the sassy Stephanie Tanner on “Full House” (1987-1995).
-
Jodie Sweetin: 2019
Jodie Sweetin attends the 2019 Nickelodeon Kids’ Choice Awards in Los Angeles. Sweetin has returned to the spotlight as a star on the “Full House” reboot “Fuller House,” which began in 2016.