Looks we love from the Oscars past and present

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If you follow inRegister on Instagram, you have probably noticed that our story each Monday morning during 2020 award season has been packed with our favorite looks from the festivities of the night before. From pink, poufy numbers to sleek, simple gowns, our team has followed all the action–and we’re assuming you have, too. These looks not only serve as talking points on the red carpet, but they set the scene for the future of fashion–creating lasting impacts that viewers remember for years, and sometimes decades, to come.

In preparation for the final show of this season, the Oscars, we asked our team to share their favorite Oscars looks of all time. Read on for our picks and comment your favorites down below:


Kelli Bozeman, managing editor

High-neck gowns have stood the test of time. These two intricate examples show that sexy doesn’t always mean showing skin.

Old: Nicole Kidman in couture Christian Dior, 1997

New: Cate Blanchett in Givenchy Couture, 2011


Riley Bienvenu Bourgeois, community writer

Flared skirts have been taken to the next level. Both of these looks are examples of elegant femininity, and we honestly can’t decide which we would opt for if we had a chance to walk down the crimson carpet.

Old: Audrey Hepburn in Givenchy, 1954

New: Gemma Chan in Valentino Couture, 2019


Madeline Gwinn, editorial intern

Playful pastels have long been a way to juxtapose the grownup elegance of red carpet fashion. Whether sleek or covered in tulle, these looks speak to the personalities of the wearers.

Past: Grace Kelly in custom Edith Head, 1955

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A few pictures of Grace in her ice blue-green dress created by Edith Head which she wore to the 1955 Oscars, where she received an Academy Award for Best Actress in The Country Girl (1954). Edith Head actually won a total of 8 Academy Awards for her Costume Design including Sabrina, Roman Holiday, All About Eve, and A Place in the Sun and she was nominated 35 times! Truly the best designer that there was and, in my opinion, ever will be! #gracekelly #gracekellystyle #princessgracekelly #princessgrace #princessgraceofmonaco #princess #hshprincessgrace #hsh #royalty #monaco #oscars1955 #oscars #academyaward #bestactress #thecountrygirl #williamholden #bingcrosby #50s #50fashion #fashion #edithhead #vintage #vintagefashion #oldhollywood #oldhollywoodglamour #oldhollywoodactress #classichollywood #goldenhollywood #goldeneraofhollywood #goldenageofhollywood

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New: Kacey Musgraves in Giambattista Valli, 2019


Liz Firesheets, account executive

Who doesn’t want a princess moment? These two looks, while vastly different, speak to a similar vision. After all, what is more timeless than dresses fit for royalty.

Old: Gwyneth Paltrow in Ralph Lauren, 1999

New: Lupita Nyong’o in Prada, 2014

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Congratulations to Lupita on her Oscar win!

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Liz Walsh, account executive

There’s no denying that sexy silhouettes will always be a go-to on the carpets of awards season. These looks take it a step further, though. With added touches like feathers and a cape, these dresses are elevated to major statements.

Old: Nicole Kidman in Gucci, 2005

New: Gwyneth Paltrow in Tom Ford, 2012


Margaret Fitzpatrick, photography intern

You can’t let the clothes wear you, right? These iconic actresses embody this motto. Their looks have stayed at the front of people’s minds not necessarily because of the styles themselves, but because of the celebrities wearing them.

Old: Audrey Hepburn in Givenchy, 1975

New: Angelia Jolie in Versace, 2012

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😍😍🔥

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