Arguably the queen of the VMAs, Britney Spears made her first appearance in 1999 in sheer black; 17 years later, she wore a similarly-colored ensemble.
Taylor Swift kicked off her storied VMA history in a blush pink dress in 2008; in 2015, she took home Video of the Year in sequined sweats.
Alicia Keys attended her first VMA's in 2004 wearing a grecian-inspired gown; last year, she appeared bare-faced.
In 2000, Beyoncé attended the ceremony with her Destiny's Child band members wearing matching leather looks; last year, she took home "Video of the Year" in a feathered couture gown.
Ariana Grande opted for a sweet floral look for her first VMA red carpet; in 2016, she opted for something a bit more mature, by Alexander Wang.
The picture of pop princess-dom, Christina Aguilera went leopard and sheer for the 1999 ceremony; by 2008, she was fully embracing the glam side of things.
Justin Bieber piled on the accessories for his first ceremony in 2010; in 2015, he opted for a more streamlined look in ripped jeans and a leather jacket.
Ciara attended her first show in 2008 wearing a silver minidress; in 2015, she took a much more fashion-forward approach in a fringed number.
Jared Leto presented at the 2006 awards wearing some serious guyliner and a white skinny scarf; nine years later, despite a new Academy Award, the actor proved he still was into his goth ways.
J.Lo showed up to the 1998 awards in a oversized cream suit and matching hat; the singer's look for the 2015 awards was far more on par to the Jennifer Lopez we know now.
Kanye West arrived at the 2004 awards in an all-white ensemble; twelve years later, he wore a similar ensemble and arrived with now-wife Kim Kardashian.
Justin Timberlake showed up with the rest of the 'Nsync gang in a leather jacket; by 2013, he had shifted to his signature fedora.
Katy Perry, who will host this year's ceremony, crafted her own ensemble for the 2008 awards; at the 2014 awards, she riffed on Britney Spears's iconic denim gown.
Lady Gaga kicked off her tradition of kooky ensembles in 2009 wearing a feathered look; in 2013, she saved her theatrics for the stage.
In a leather mini and trailing braid, Kesha made her VMA debut in 2010; in 2014, she toned down the look with a pastel gown and matching hair.
Madonna kicked off the inaugural ceremony in 1984; in 2009, she returned in a subdued black suit.
A year before her iconic lavendar catsuit, L'il Kim matched Lisa "Left Eye" Lopez at the 1997 awards; the rapper let her boots do the talking in 2013.
Gwen Stefani attended the 1997 awards with her No Doubt bandmates; in 2014, she was solo and donning shocking pink.
Miley Cyrus arrived at the 2008 awards in a modest metallic dress; in 2015, her look was still metallic but definitely not modest.
Pink, who will receive this year's Video Vanguard Award, took home her first moon-man in 2001; the singer arrived at the 2012 awards in a metallic gown.
Rihanna was a fresh-faced and little-known singer when she attended the show in 2005; last year, she recieved the Video Vanguard award.
Demi Lovato attended the 2011 awards in a sequined minidress; four years later, she returned wearing a similar ensemble.
Selena Gomez made her VMA debut in 2011 in a high-low black dress; in 2015, she was super sophisticated in navy Calvin Klein.
Solange arrived at the 2001 awards in an ensemble she'd likely not be caught in today; the singer was much more in tune with her current sartorial standard by 2014.