Over her two-plus decades in the spotlight, Mandy Moore has grown from teen pop princess to critically acclaimed actress. Her sense of style has joined her on this journey of growth.
From the long skirts, shiny fabrics and questionable accessories of the early 2000s to the bold gowns and neutral ensembles she’s sported in more recent years, Moore’s red carpet looks are often daring.
We’ve rounded up 63 photos of Mandy Moore’s style evolution, from bubble gum pop to designer chic.
1999 Moore at the 10th Annual Billboard Music Awards.
2000 Moore at the Kids' Choice Awards at the Hollywood Bowl.
2000 Moore at the MTV Video Music Awards at Radio City Music Hall in New York City.
2000 Mandy Moore at Summer Music Mania 2000 in Jacksonville, Florida.
2001 Moore at the "MTV ICON: Janet Jackson" show taping at Sony Pictures Studios in Los Angeles.
2001 Moore at an album event at the FYE store at at Rockefeller Plaza in New York City.
2001 Moore at the World Premiere of "Ocean's Eleven" at Mann's Village Theatre in Westwood.
2002 Moore at Nickelodeon's 15th Annual Kids' Choice Awards at Barker Hangar in Santa Monica, California.
2002 Moore at the 2002 MTV Movie Awards at The Shrine Auditorium in Los Angeles.
2002 Moore at the Big Brothers/Big Sisters of Greater Los Angeles Annual "Rising Stars" Gala.
2003 Moore at the Elton John AIDS Foundation's 11th Annual Oscar party at The Marquee in West Hollywood.
2003 Moore at the "How to Deal" New York premiere at Loews Lincoln Square.
2003 Moore at the 2003 Billboard Music Awards at MGM Grand Garden Arena in Las Vegas.
2004 Moore at the "Chasing Liberty" world premiere at Grauman's Chinese Theater in Hollywood.
2004 Moore at the 30th annual People's Choice Awards at Pasadena Civic Auditorium in Pasadena.
2004 Moore at the 2004 MTV Video Music Awards at the American Airlines Arena in Miami.
2005 Moore at the 2005 CFDA Fashion Awards at the New York Public Library in New York City.
2005 Moore during the Lucky Magazine Hosts Miss Davenporte Trunk Show at Ron Herman in Los Angeles.
2006 Moore at the Focus Features, NBC Universal Television Group and Universal Pictures Golden Globes After Party at the Beverly Hilton Hotel in Beverly Hills.
2006 Moore at the Conde Nast Traveler Hot List Party at Buddha Bar in New York City.
2007 Moore at the 49th Annual Grammy Awards at the Staples Center in Los Angeles.
2007 Moore at the 14th Annual Entertainment Industry Foundation Revlon Run/Walk For Women at Los Angeles Memorial Coliseum.
2007 Moore at the "License to Wed" Los Angeles premiere at Cinerama Dome in Hollywood.
2008 Moore at the 11th annual "Fresh Faces in Fashion" at the Peterson Automotive Museum in Los Angeles.
2009 Moore at the launch party for "LATISSE" in West Hollywood.
2009 Moore at the Madison & Diavolina Launch Party in Los Angeles.
2009 Moore at the third annual amfAR Cinema Against AIDS event in Dubai.
2010 Moore at the Los Angeles premiere of "Tangled" at the El Capitan Theatre in Hollywood.
2010 Moore at the 2010 American Music Awards at Nokia Theatre in Los Angeles.
2011 Moore at the 16th annual Critics' Choice Movie Awards at the Hollywood Palladium in Los Angeles.
2011 Moore at the 68th annual Golden Globe Awards at The Beverly Hilton Hotel in Beverly Hills.
2011 Moore at the U.K. premiere of "Tangled" in London.
2011 Moore at the 83rd annual Academy Awards at the Kodak Theatre in Hollywood.
2012 Moore at Billy Reid's spring 2013 fashion show during Mercedes-Benz Fashion Week at Eyebeam in New York City.
2012 Moore at Boy and Girl by Band of Outsiders Spring at the St. John's Center Studios in New York City.
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This article originally appeared on HuffPost and has been updated.