Fashion Moments Through the Years
Matthew Perez
Updated on March 20, 2026
Natasha Lyonne has been making waves since she was a child actress. She first got her big break when she was cast of “Pee-wee’s Playhouse” and then went on to star as Meryl Streep’s niece in the dramedy “Heartburn.” Nowadays, her fans know her for starring in “Orange Is the New Black,” “Russian Doll” and “Poker Face.”
In the late ‘90s, Lyonne became a fixture on Hollywood event red carpets, from movie premieres to galas. Throughout the decades, her style has evolved from that of a young Hollywood starlet to that of an established actress with a clear penchant for edgy all-black ensembles. Outside of stage, television and film, she’s also starred in ad campaigns for Old Navy, COS and Moose Knuckles.
Here, WWD takes a closer look at Lyonne’s style through the years.
Natasha Lyonne, 1998
Image Credit: Ron Galella Collection via Getty Natasha Lyonne during “Everyone Says I Love You” New York City in 1997.
Natasha Lyonne, 1998
Image Credit: WireImage Natasha Lyonne and Edward Furlong at the “American Pie” premiere in 1998.
Natasha Lyonne, 2000
Image Credit: FilmMagic, Inc Natasha Lyonne during 2000 Independent Spirit Awards in Santa Monica, California.
Natasha Lyonne, 2000
Image Credit: WireImage Natasha Lyonne at Outfest in 2000.
Natasha Lyonne, 2002
Image Credit: WireImage Natasha Lyonne & Tara Subkoff during 2002 Tribeca Film Festival “About A Boy” premiere at Tribeca Performing Arts Center in New York City.
Natasha Lyonne, 2003
Image Credit: WireImage Natasha Lyonne during Hollywood Takes a Bite Out of The Big Apple as Playstation2 and Guy Oseary Celebrate The 2003 VMAs at Four Seasons Restaurant in New York City.
Natasha Lyonne, 2004
Image Credit: FilmMagic Natasha Lyonne during 2004 Audi Never Follow Gala at Manhattan Center in New York City.
Natasha Lyonne, 2006
Image Credit: WireImage Natasha Lyonne at the Privilege in West Hollywood, California, for Paris hilton’s CD launch in 2006.
Natasha Lyonne, 2007
Image Credit: WireImage Natasha Lyonne at the The Orpheum Theatre in Los Angeles for the “Grindhouse” premiere in 2007.
Natasha Lyonne, 2008
Image Credit: Getty Images Actors Natasha Lyonne and James Ransone attend the premiere of the fifth season of “Entourage” presented by HBO at the Ziegfeld Theater on Sept. 3, 2008 in New York City.
Natasha Lyonne, 2009
Image Credit: WireImage Actress Natasha Lyonne attends the after party for the opening night of “Love, Loss and What I Wore” at Bryant Park Grill on Oct. 1, 2009, in New York City.
Natasha Lyonne, 2010
Image Credit: Getty Images Natasha Lyonne attends the 2010 Dress For Success Worldwide Gala at the Grand Hyatt Hotel on April 20, 2010, in New York City.
Natasha Lyonne, 2011
Image Credit: WireImage Actress Natasha Lyonne attends Rosie’s Building Dreams for Kids Gala at The New York Marriott Marquis on Sept. 19, 2011, in New York City.
Natasha Lyonne, 2012
Image Credit: Getty Images Actress Natasha Lyonne attends the 78th annual Drama League Awards Ceremony and Luncheon at the Marriott Marquis Times Square on May 18, 2012, in New York City.
Natasha Lyonne, 2013
Image Credit: WireImage Actress Natasha Lyonne attends Cinema Society Presents The World Premiere Of “Girls” Season 2at NYU Skirball Center on Jan. 9, 2013, in New York City.
Natasha Lyonne, 2014
Image Credit: WireImage Natasha Lyonne attends The Weinstein Company & Netflix 2014 Golden Globes After Party held at The Beverly Hilton Hotel on Jan. 12, 2014, in Beverly Hills, California.
Natasha Lyonne, 2015
Image Credit: Getty Images Actress Natasha Lyonne attends the 72nd Annual Golden Globe Awards at The Beverly Hilton Hotel on Jan. 11, 2015 in Beverly Hills, California.
Natasha Lyonne, 2016
Image Credit: WireImage Actors Natasha Lyonne (L) and Fred Armisen attend the “Zoolander 2” World Premiere at Alice Tully Hall on Feb. 9, 2016, in New York City.
Natasha Lyonne, 2017
Image Credit: Getty Images Actor Natasha Lyonne attends the 2017 Film Independent Spirit Awards at the Santa Monica Pier on Feb. 25, 2017, in Santa Monica, California.
Natasha Lyonne, 2018
Image Credit: Getty Images Actor Natasha Lyonne attends the 24th Annual Screen Actors Guild Awards at The Shrine Auditorium on Jan. 21, 2018, in Los Angeles.
Natasha Lyonne, 2019
Image Credit: Getty Images Natasha Lyonne attends the 61st Annual Grammy Awards at Staples Center on Feb. 10, 2019, in Los Angeles.
Natasha Lyonne, 2020
Image Credit: Getty Images Natasha Lyonne attends the 77th Annual Golden Globe Awards at The Beverly Hilton Hotel on Jan. 5, 2020, in Beverly Hills, California.
Natasha Lyonne, 2022
Image Credit: Getty Images Natasha Lyonne attends the 74th Annual Directors Guild Of America Awards at The Beverly Hilton on March 12, 2022, in Beverly Hills, California.
Natasha Lyonne, 2023
Image Credit: Patrick McMullan via Getty Image Natasha Lyonne attends 2023 TIME100 Gala at Jazz at Lincoln Center on April 26 New York City.
