Christina Aguilera-2000
The singer sparkled (and showed off her love for butterflies) in a jeweled Versace dress while winning the Best New Artist Award at the 2000 Grammys.
Christina Aguilera-2001
Christina looked a lot more scandalous the following year in a pirate-inspired dress with a high slit, a flirty cleavage line, and long braids. This looks like a prelude to the "Dirty" era...
Christina Aguilera-2006
Is this a modern-day Marilyn Monroe? Christina looked every part the Old Hollywood vixen in a silky white halter gown by Roberto Cavalli and glam curls. She's one step away from a nip slip!
Madonna-1999
At the 1999 Grammys, Madonna pulled off her best Kabuki style in a Geisha-inspired getup with stick-straight hair and matching boots.
Madonna-2006
It may have been decades since she did the infamous Madonna bustier, but we see a hint of it coming back in her halter dress at the 2006 Grammys, which she wore over black leggings and boots.
Madonna-2014
At the 2014 Grammys, Madonna went all-out in a black tux with a stylish hat, bowtie, and a cane to accessorize!
Taylor Swift-2008
T-Swift looked ready for a high school prom at the 2008 Grammys in a long, lavender-colored Sandy Spika gown fit for a debutante.
Taylor Swift-2009
Amazing how much can change in one year! At the 2009 Grammys, Taylor transformed into a Grecian goddess with an open-back Kaufmanfranco gown and an elegant updo.
Taylor Swift-2014
The singer debuted her most sophisticated and grown-up look yet at the 2014 Grammys, wearing a sparkly Gucci gown with subtle sheer mesh panels and a low ponytail.
Taylor Swift - 2015
The singer looked like a dream in a teal-colored Elie Saab gown that showed plenty of pour (and leg) along with magenta heels.
Celine Dion-1995
At the 1995 Grammys, the singer looked like she was a bridesmaid at an '80s wedding with her long sparkly gown and a short hairstyle to match!
Celine Dion-1996
The singer proved that she was one part business and one part party with her formal suit and a vest that exposed part of her belly at the 1996 Grammys!
Gwen Stefani-1997
Gwen looked super comfy in a silky, nightgown-inspired enesemble at the 1997 Grammys, which she wore with her trademark Bindi.
Gwen Stefani-2001
Several years later, Gwen showed up at the 2001 Grammys in a poufy red gown and blonde curls, sharing a more grown-up and feminine side with the world.
Gwen Stefani-2006
At the 2006 Grammys, Gwen paraded her baby bump in a multi-color leopard gown that looked like it was dipped in several shades of green tie-dye at the bottom. The color and style also reminds us a lot of her L.A.M.B. line of bags and accessories...
Gwen Stefani - 2015
The singer looked rockin' with her poufy 'do and her artistic black pantsuit by Atelier Versace.

