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 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...
Several years later at the 2004 Grammys, Christina showed off her burlesque side with a feathered neckline, Old Hollywood ringlets, and more dramatic makeup.
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!
At the 1999 Grammys, Madonna pulled off her best Kabuki style in a Geisha-inspired getup with stick-straight hair and matching boots.
The singer looked a lot more toned-down while presenting an award at the 2004 Grammys in a ruffled pink dress with black boots. Very Real Housewives of Orange County, if you ask us!
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.
At the 2014 Grammys, Madonna went all-out in a black tux with a stylish hat, bowtie, and a cane to accessorize!
The singer had us seeing red with her Givenchy Matador outfit at the 2015 Grammys. Even her performance was Matador-themed, complete with dancing bulls!
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.
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 looked every bit the sparkly mermaid in another Kaufman Franco gown—this time a shimmering blue shade for the 2010 Grammys.
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.
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 wore a provocative see-through black gown at the 1993 Grammys that showed a lot more than we were expecting to see—underwear and all!
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!
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!
At the 2010 Grammys, Celine dazzled in an embellished dress featuring multiple neutral shades and adornments, poufy sheer sleeves, and strappy heels.
Gwen looked super comfy in a silky, nightgown-inspired enesemble at the 1997 Grammys, which she wore with her trademark Bindi.
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 showed some extra skin at the 2005 Grammys, wearing a see-through black mini-gown that showed a hint of her underwear and was accessorized by black ribbon and a teased updo.
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...
The singer looked rockin' with her poufy 'do and her artistic black pantsuit by Atelier Versace.
Back in the Destiny's Child era, Beyoncé and her fellow group members looked like professional belly dancers in their matching sparkly green dresses.