Here's How 27 Celebrities Have Transformed From Their Very First Oscars Vs. 2026

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Another year, another awards season in the books — last night was finally the 2026 Oscars, and celebs didn't disappoint with their looks. Here's a look at 26 celebs this year compared to what they wore at their very first Oscars:

1. Leonardo DiCaprio at his first Oscars in 1994:

A person in a tuxedo with a bow tie and a red ribbon, standing on a dimly lit red carpet

Leonardo DiCaprio at the 2026 Oscars:

A celebrity in a classic black tuxedo and bow tie poses on the red carpet at an awards event

2. Melissa McCarthy at her first Oscars in 2012:

A person in an elegant, flowing gown poses confidently on the red carpet at a celebrity event, holding a small clutch bag

Melissa McCarthy at the 2026 Oscars:

A person poses on the red carpet, wearing a floor-length gown with intricate beading and holding a clutch

3. Michael B. Jordan at his first Oscars in 2014:

Person in a sleek suit smiles on the red carpet, surrounded by photographers and onlookers, showcasing an elegant and polished look

Michael B. Jordan at the 2026 Oscars:

A person stands on the red carpet holding an Oscar, wearing a sleek, buttoned-up black suit

4. Zinzi Evans and Ryan Coogler at their first Oscars in 2019:

A couple poses on a red carpet. The woman wears an elegant black strapless gown, while the man dons a gray suit with a patterned scarf

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Zinzi Evans and Ryan Coogler at the 2026 Oscars:

Two individuals stand on a red carpet; one wears an elegant black gown, the other a classic tuxedo

5. Amy Madigan and Ed Harris at their first Oscars in 1986:

A man and woman pose on a red carpet. He wears a tuxedo; she wears an elegant black gown with a statement necklace

Amy Madigan and Ed Harris at the 2026 Oscars:

Two individuals pose at a formal event. One holds a statue. The other is in a tuxedo. Both wear glasses

6. Nicole Kidman at her first Oscars in 1991:

A woman with curly hair stands on a red carpet, wearing an elegant, fitted velvet dress with sequined details

Nicole Kidman at the 2026 Oscars:

Celebrity in a strapless, embellished gown with feathered details poses with hands on hips at a formal event

7. Emma Stone at her first Oscars in 2012:

Actor in an elegant gown on the red carpet, featuring a high-neck and ruffled details, surrounded by event attendees

Emma Stone at the 2026 Oscars:

A person on the red carpet wears an elegant, shimmering gown with cap sleeves

8. Kathy Bates at her first Oscars in 1991:

A celebrity smiles while holding an award trophy, dressed in an embellished, elegant outfit

Kathy Bates at the 2026 Oscars:

A person on the red carpet wearing an elegant, embellished gown, holding a clutch, at an Oscars event

9. Jimmy Kimmel at his first Oscars in 2017:

A person in a tuxedo stands on stage holding a microphone, appearing to speak during a formal event

Jimmy Kimmel at the 2026 Oscars:

A man in a tuxedo speaks on stage, holding an envelope, likely at a formal or award event

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10. Pedro Pascal at his first Oscars in 2023:

A person in a sleek black suit with a high-collared white shirt poses on a red carpet

Pedro Pascal at the 2026 Oscars:

Person in formal attire with a unique textured design on their shirt, posing on a red carpet

11. Barbra Streisand at her first Oscars in 1969:

A person in a sheer, sequined dress with white collar and cuffs holds an award statue on a stage

Barbra Streisand at the 2026 Oscars:

Person in an off-the-shoulder dress, wearing sunglasses and a necklace, stands at a podium, holding a card during a formal event

12. Anne Hathaway at her first Oscars in 2007:

Person in a strapless lace gown with a large bow detail stands on a red carpet, surrounded by a crowd in formal attire

Anne Hathaway at the 2026 Oscars:

Woman in floral gown with gloves on red carpet, smiling, standing against a backdrop with "Oscars" text

13. Anna Wintour at the Oscars in 2015:

Person on the red carpet wearing a chic fur stole over an elegant, sleeveless dress, accessorized with a statement necklace

Anna Wintour at the 2026 Oscars:

Person on red carpet in stylish black patterned jacket, statement necklace, and sunglasses

14. Goldie Hawn at her first Oscars in 1976:

Two individuals in formal attire stand onstage. The woman wears a sparkly gown with spaghetti straps, and the man is in a tuxedo

Goldie Hawn at the 2026 Oscars:

A celebrity in a sparkling black gown with lace details and matching gloves poses on a red carpet

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15. Kate Hudson at her first Oscars in 2001:

Person in an elegant gown with sheer details poses on the red carpet amidst photographers and attendees

Kate Hudson at the 2026 Oscars:

A celebrity poses on the red carpet in a sparkling strapless gown with a peplum detail, accessorized with a necklace and earrings

16. Kristen Wiig at her first Oscars in 2012:

Person in an elegant, tiered gown poses at an event with a large sign in the background

Kristen Wiig at the 2026 Oscars:

A person in an elegant, sleeveless black and silver gown poses on a carpet at a celebrity event

17. Timothée Chalamet at his first Oscars in 2018:

Person in a white tuxedo with a bow tie on a red carpet with geometric backdrop

Timothée Chalamet at the 2026 Oscars:

Person in a tailored suit with wide-leg pants and sunglasses stands on a red carpet at a celebrity event

18. Demi Moore at her first Oscars in 1992:

Woman with short styled hair in an elegant floral lace dress, attending a formal event with a backdrop featuring an Oscar statue

Demi Moore at the 2026 Oscars:

A woman on the red carpet wears an elaborate dress with feather-like details resembling dark plumage

19. Billy Crystal presenting at the 1997 Oscars:

A person in a tuxedo gestures expressively on a stage, appearing to perform or speak animatedly

Billy Crystal at the 2026 Oscars:

An individual in formal attire speaks animatedly on a stage, gesturing with open hands

20. Ava DuVernay at her first Oscars in 2015:

Person in an elegant gown with embellished details on a red carpet

Ava DuVernay at the 2026 Oscars:

Person in an elegant off-the-shoulder gown poses on a red carpet at an award event backdrop

21. Heidi Klum at her first Oscars in 2008:

Celebrity on a red carpet in an elegant, strapless gown with a dramatic train, posing confidently for photographers

Heidi Klum at the 2026 Oscars:

Celebrity in an embellished strapless gown poses on the red carpet, hands on hips, smiling at the event

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22. Gwyneth Paltrow at her first Oscars in 1999:

Person in elegant gown with spaghetti straps and full skirt on a red carpet

Gwyneth Paltrow at the 2026 Oscars:

Person in a sleek, floor-length, strapless gown poses at an event with "OSCARS" in the background

23. Zoe Saldaña at her first Oscars in 2010:

Actor on the red carpet in a strapless gown with a sequined bodice and layered ruffle skirt

Zoe Saldaña at the 2026 Oscars:

Person in an elegant floor-length gown with lace details stands on a red carpet at a formal event

24. Ethan Hawke at his first Oscars in 1999:

A person on the red carpet wearing a classic tuxedo with a bow tie, smiling at the camera

Ethan Hawke at the 2026 Oscars:

Person on red carpet in formal black suit with long coat and bowtie, at an event with "OSCARS" in the background

25. Delroy Lindo and Nashormeh Lindo at the 2008 Oscars:

Two people pose on a red carpet. The person on the right wears a tailored suit and patterned scarf. The person on the left wears a shawl and skirt

Delroy Lindo and Nashormeh Lindo at the 2026 Oscars:

A couple poses on the red carpet. The woman wears a vibrant, patterned dress, and the man is in a black suit with a white shirt and blue tie

26. Adrien Brody at his first Oscars in 2003:

Person in a dark tailored suit holding an award statuette triumphantly, standing in front of a floral backdrop

Adrien Brody at the 2026 Oscars:

Person in a classic black tuxedo with a unique lapel adornment, posing on a red carpet at a formal event

27. Spike Lee at his first Oscars in 1992:

Person in formal attire with glasses and a white bow tie at a prestigious event

Spike Lee at the 2026 Oscars:

Person in a brown plaid suit, purple hat, and bow tie on a red carpet, holding a bag. They're wearing white shoes and glasses

Check out the rest of our Oscars coverage here..

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