Britney Spears’ Fashion Evolution
December 2, 2019
Penelope Trent

From the minute she burst into the scene with Baby One More Time in 1998, Britney Spears has graced us with many incredible looks. For over two decades, Spears has yet to disappoint us. In honor of Spears’ birthday today, I have decided to check how far has style has come since she started her journey in Hollywood.


There is a lot to unpack here, so hold tight and let’s take a trip down the fashion evolution lane of the princess of pop.


October 1998



Going down in history as one of the most iconic outfits ever, Britney Spears wore a schoolgirl outfit and two braids.


January 1999


Getty Images/ WireImage/ Kevin.Mazur/INACTIVE


Attending the 1999 American Music Awards, Spears wore a pastel pink gown.


August 1999


Getty Images/ WireImage/ Barry King


Spears wore a light pink tank top and sparkly pink pants to the 1999 Teen Choice Awards.

December 1999


Getty Images/ WireImage/ Steve Granitz


To the 1999 Billboard Music Awards, the starlet wore a lilac gown and white shawl.


February 2000


Getty Images/ WireImage/ Kevin.Mazur/INACTIVE


Spears attended a pre-Grammy party in a sparkly, silver crop top and printed satin pants.


Getty Images/ WireImage/ KMazur


A day after, at the actual awards show, Spears channeled Old Hollywood in sleek white Randolph Duke gown and Oscar de la Renta fur cover.


August 2000


Getty Images/ WireImage/ Barry King


The superstar wore a pink, fringed mini-dress to the 2000 Teen Choice Awards.


December 2000


Getty Images/ WireImage/ SGranitz


At the 2000 Billboard Music Awards, Spears wore a pink and orange ensemble.


January 2001


Getty Images/ WireImage/ Jeffrey Mayer


Attending the American Music Awards with then-boyfriend, Justin Timberlake, the couple went in a matching denim theme.


September 2001


Getty Images/ WireImage/ KMazur


Britney wore a revealing black lace Dolce & Gabbana dress to the 2001 MTV Video Music Awards.


February 2002


Getty Images/ WireImage/ KMazur


To the 2002 Grammy Awards, the singer wore a red gown, which she matched to voluminous curls.


March 2002


Getty Images/ Entertainment/ Anthony Harvey


Attending the London premiere of her 2002 film, Crossroads, the starlet wore a sparkly silver dress.


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