1Jennifer Lopez
Getty ImagesEver the '90s icon, J.Lo sported a button-up shift dress with a pair of high heel mules and a perm at the premiere of Mi Vida Loca in 1994.
2Blake Lively
Getty ImagesSkyrocketing to fame through her role in The Sisterhood of the Travelling Pants, it's kind of fitting that Blake wore a pair of worn-in jeans to Nickelodeon's 18th Annual Kids Choice Awards in 2005.
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3Rihanna
Getty ImagesWhoa, remember when midriff tops were all the rage on the red carpet? Here's Rihanna sporting the look like a total pro at the 2005 Teen People Listening Lounge.
4Kourtney and Kim Kardashian
Getty ImagesThe Kardashian gals opted for matching white cocktail dresses and sleek blowouts at E! Entertainment Television's 2005 Summer Splash Event.
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5Selena Gomez
Getty ImagesSelena opted for an all-black combo with cute polka dot flats and one of the iconic early noughties quiffs in her hair at the Shrek the Third premiere in 2007.
6Taylor Swift
Getty ImagesHere's Taylor rocking a very boho waterfall hem dress and wavy strands 2006 CMT Music Awards - what a time to be alive.
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7Jessica Alba
J. VespaJessica went for a statement sleeveless floral number at the 27th Annual People's Choice Awards in 2001 and even matched her lipstick to her dress, which is dedication.
8Jennifer Aniston
Getty ImagesRachel Green-era Jennifer rocked high-waisted Mum jeans and an oversized boyfriend shirt at The NBC Stars Party in 1990.
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9Miley Cyrus
Getty ImagesMiley Cyrus wore our go-to outfit for friends' birthday parties for the Over The Hedge premiere in 2006.
10Reese Witherspoon
Getty ImagesReese wore a snazzy floral motif design for the premiere of The Man In The Moon in 1991.
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11Kendall Jenner
Getty ImagesLook how small Kendall Jenner is at the world premiere of Mulan in 1998! That fringe alone deserves a round of applause.
12Lady Gaga
Getty ImagesBold from the start, Lady Gaga went theatrical AF at the 2009 MTV Video Music Awards.
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13Ariana Grande
Getty ImagesA red-haired Ariana sported a body con mini and a highlighter pink mani for the The Lovely Bones premiere in 2009.
14Jennifer Lawrence
Getty ImagesJ.Law was all about the statement A-line dress with a perfectly undone up-do at the 15th Annual Movieguide Faith and Values Awards in 2007.
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15Lizzo
Getty ImagesLizzo donned her jeans and a nice, Versace-style, top at the Roc Nation Grammy Brunch in 2015.
16Dua Lipa
Getty ImagesDua Lipa was in on the shift dress trend way back in 2016, layering it underneath a statement leather jacket for the Warner Music Group's annual Grammy celebration in 2016.
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17Hailey Bieber
Getty ImagesBaby Hailey at The Flintstones in Viva Rock Vegas Universal City Premiere in 2000 is the only thing I needed to see today. Honestly though, how adorable is she?
18Anne Hathaway
Getty ImagesAnne oozes Princess Diaries vibes (post-makeover, ofc), wearing straight-leg trousers and a pastel pink jumper at the FOX TV Up Front Celebration in 1999.
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19Gigi Hadid
Alberto E. Rodriguez//Getty ImagesJust like Anne, Gigi also chose trousers over a dress for her first red carpet, wearing these metallic eye-catchers at the 2012 Heart Foundation Gala.
20Zendaya
Getty ImagesLittle Zendaya went all-out for the premiere of Megamind in 2010, even going so far as wearing on-theme costume makeup.

Natasha Harding is the former Fashion Editor (Digital & Print) at Cosmopolitan & Women's Health UK. Working in fashion journalism for just under ten years, sheâs covered over 30 international fashion weeks, hundreds of red carpets and religiously scours the runway every season to create the brandâs bi-annual trend report. Joining Cosmopolitan back in Australia, Natasha moved to London a few years ago and is now the resident expert for celebrity style and industry news, fashion features and e-commerce. Follow Natasha on Instagram
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