Oscars 2020: From Angelina Jolie to Lady Gaga – 16 of the best dresses of all time

By Liz Connor, PA

The Oscars has forever been the biggest night of Hollywood glamour. After all, it’s the one event where what you wear is just as important as your acceptance speech, and the right dress can go down in history

From Angelina Jolie’s famous ‘leg’ moment to the dress that cemented Lupita Nyong’o’s status as a style icon, take a moment to appreciate some of the most memorable dresses in Oscars history…

1. Gwyneth Paltrow, 1999

Gwyneth Paltrow with her Oscar for Best Actress (Peter Jordan/PA)

Paltrow caused a major stir at the 1999 awards ceremony, not just for the teary delivery of her Best Actress acceptance speech, but for the floor-skimming, Ralph Lauren dress she wore on the red carpet.

2. Nicole Kidman, 2000

Australian actress Nicole Kidman with Tom Cruise (Michael Crabtree/PA)

Queen of the red carpet, Kidman turned heads at the Millennium Oscars when she upstaged then-husband Tom Cruise in this slinky number by Dior.

3. Halle Berry, 2002

Halle Berry arriving at the 74th Annual Academy Awards (Myung Jung Kim/PA)

We’re still obsessed with this Elie Saab mesh and embroidery dress Berry famously wore. The contrast between the tulle skirting and net body was definitely a style risk, but the American actress pulled it off perfectly.

4. Charlize Theron, 2004

Actress Charlize Theron arrives at the Kodak Theatre in Los Angeles for the 76th Academy Awards (Ian West/PA)

2004 wasn’t a great year for fashion, but Charlize Theron managed to transcend the numerous naff trends in this stunning Tom Ford for Gucci dress. The actress pulled the entire look together with a pair of Chopard earrings and a Lana Marks bag.

5. Marion Cotillard, 2008

Marion Cotillard arrives for the 80th Academy Awards (Oscars) at the Kodak Theatre, Los Angeles (Ian West/PA)

While others played it safe at the 2008 awards, Cotillard made an impact in this Jean Paul Gaultier mermaid dress, that looked as though it was made from fish scales.

6. Anne Hathaway, 2009

Anne Hathaway arriving for the 81st Academy Awards at the Kodak Theatre, Los Angeles (Ian West/PA)

Anne Hathaway looked as regal as the Oscars statue itself in this dazzling Armani Privé gown with thousands of tiny embellishments.

7. Zoe Saldana, 2010

Zoe Saldana arriving for the 82nd Academy Awards at the Kodak Theatre, Los Angeles (Ian West/PA)

An ombre ruffled dress isn’t the easiest look to pull off, but Zoe Saldana had us all clamouring to wear more lilac after she donned this Givenchy Haute Couture gown.

8. Meryl Streep, 2012

Meryl Streep arriving for the 84th Academy Awards at the Kodak Theatre, Los Angeles (Ian West/PA)

Streep proved she’s the golden girl of the Academy Awards in this gilded wrap dress with a barely-there waist belt.

9. Michelle Williams, 2012

Michelle Williams arriving for the 84th Academy Awards at the Kodak Theatre, Los Angeles (Ian West/PA)

The peplum had a major moment back in 2012, and Williams schooled us all in this red tulle Louis Vuitton gown.

10. Angelina Jolie, 2012

Angelina Jolie arriving for the 84th Academy Awards at the Kodak Theatre, Los Angeles (Ian West/PA)

Who could forget Angelina Jolie’s thigh-split dress that spawned a thousand memes? The iconic leg-baring 2012 Oscars gown was designed by Versace and became an instant viral sensation.

11. Jessica Chastain, 2014

Jessica Chastain arriving for the 85th Academy Awards at the Dolby Theatre, Los Angeles (Ian West/PA)

Sparkles, a sweetheart neckline and a gorgeously flattering fit. What’s not to love about Jessica Chastain’s Armani Prive gown?

12. Lupita Nyong’o, 2014

Lupita Nyong’o with her Best Supporting Actress award in the press room of the 86th Academy Awards held at the Dolby Theatre in Hollywood, Los Angeles, CA, USA, March 2, 2014 (Ian West/PA)

The 2014 Oscars belonged to Lupita Nyong’o. Not only did she scoop the award for Best Supporting Actress, she was also our best-dressed star of the night in this incredible Prada dress.

13. Zendaya, 2015

Zendaya arriving at the 87th Academy Awards held at the Dolby Theatre in Hollywood, Los Angeles, CA, USA, February 22, 2015 (Ian West/PA)

Zendaya proved she and British designer Vivienne Westwood were the perfect style match when she made her Oscars debut in this gorgeous silk gown.

14. Cate Blanchett, 2016

Cate Blanchett arriving at the 88th Academy Awards held at the Dolby Theatre in Hollywood, Los Angeles, CA, USA, February 28, 2016 (Ian West/PA)

Aussie actress Cate Blanchett looked statuesque in this Armani Privé turquoise gown with floral embellishments.

15. Saoirse Ronan, 2018

Saoirse Ronan arriving at the Vanity Fair Oscar Party held in Beverly Hills, Los Angeles, USA.

Oscars gowns don’t have to be oversized and dramatic to be great. This simple strapless dress, worn by Saoirse Ronan, is one of our all-time faves thanks to its understated elegance.

16. Lady Gaga, 2019

Lady Gaga with her Oscar for Best Original Song attending the Vanity Fair Oscar Party held at the Wallis Annenberg Center for the Performing Arts in Beverly Hills, Los Angeles, California, USA (Ian West/PA)

Lady Gaga made history in 2019 after becoming the first person to win an Oscar, Grammy, BAFTA and Golden Globe within a single year.

Aside from her incredible awards sweep, everyone was talking about the fact Gaga broke tradition by wearing a dress with practical pockets on the Oscars red carpet.