Oscar’s Best Dressed of All Time


Oscar’s Best Dressed of All Time

Our Picks for Best Dressed at the Oscars

Here at Skip, you know just how much we care for fashion and all things glamorous. So what better event to ogle all of the gorgeous dresses donned by Hollywood stars than the Oscars? The biggest names in entertainment make sure that they’re dressed to the nines when they step out on the red carpet. But no red carpet brings forth glamour, ground-breaking designer creations and true style like the Oscars. 2015 will see the 87th Annual Academy Awards take place on 22 February 2015. Over the years we’ve seen the top designers’ most incredible garments steal the show. We’ve decided to give you a preview of the exciting things that you can expect at this year’s Oscars with our list of the 20 best-dressed stars in the history of The Academy Awards.

20. Audrey Hepburn

We’ll kick off with the furthest back - the iconic moment when Audrey Hepburn won the Best Actress Oscar for her role in the film Roman Holiday in the 50s. Her dress was designed by Hubert de Givenchy and she went on to become his muse. The delicate flowers adorning the fabric flattered her tiny features, making her look innocent, yet striking and sexy, winning hearts all over the fashion industry.

19. Geena Davis

At the 64th Academy Awards, Geena Davis wore a ruffled minidress designed by costume designers Ruth Meyers and Bill Hargate. We love the daring and experimental nature of her outfit. This cocktail bride look was definitely a memorable red carpet moment.

18. Sandra Bullock

Best Actress Oscar winner, Sandra Bullock, didn't just score a little gold statue; she triumphed on the red carpet too. Oozing elegance, the star wowed in a floor-skimming metallic Marchesa gown that was perfectly set off with a hot pink pout and slick, side-swept locks. All-in-all, Sandra won on every count!


17. Halle Berry

Berry wore a unique dress by Elie Saab for the 2002 Oscars. With a satin train and some strategically placed embroidery, she wowed the red carpet onlookers. Later in the evening, she was awarded the Best Actress Oscar for her performance in Monster’s Ball. This saw her become the first African-American actress to win the award, and her speech covered racism in the industry.

16. Jennifer Lopez

Jennifer Lopez arrived for the 73rd Annual Academy Awards wearing a Chanel dress that revealed the sexy silhouette of her breasts by way of a gorgeous lace bodice. The ivory and olive colour was absolutely perfect with her skin tone.

15. Keira Knightley

Vera Wang pulled out all the stops for Keira Knightley taffeta asymmetrical gown that she wore to the 2006 Oscars. This iconic red carpet fashion moment went on to raise £4 301 for charity when Knightley later donated the sensational dress to Oxfam. Who said fashion was just for show?

14. Angelina Jolie

In 2004, a gorgeous Angelina Jolie stepped out in a plunging, white-satin gown with matching wrap from Marc Bouwer. Matched with fabulous jewellery, Jolie made her appearance at the 76th Academy Awards one that will be remember for a long time.


13. Salma Hayek

The Spanish beauty looked absolutely flawless in a one-shoulder, aquamarine and satin Versace gown. This woman would look good in dishcloths though, but her 2006 red carpet outfit is one to remember.

12. Marion Cotillard

Marion Cotillard was a vision in white in a Jean Paul Gaultier gown at the 80th Academy Awards. The fin-like detail must have satisfied her childhood mermaid wishes as well.

11. Halle Berry

Dressed so nice, we’ve got her twice! This time styled by Phillip Bloch, Berry looked fabulous in her gold, Elie Saab dress. The $20 000 glittering gown, which she thought to be too transparent, was a sensational hit.


10. Meryl Streep

For the 84th Academy Awards, Meryl Streep’s floor-length gold wraparound Lanvin gown with a plunging neckline was elegant and stylish. We absolutely love it.

9. Kate Hudson

Kate Hudson walked the red carpet in a breath-taking Versace gown for the 2003 Oscars. The intricate design of hand-made gold chiffon silk took 500 hours to create and was worth all the effort.


8. Rachel Weisz

Rachel Weisz returned to the Oscars a year after winning Best Supporting Actress, this time to present an award. She wore an elegant champagne Vera Wang dress with exquisite diamante detail on the bust and a short train with plaited satin and tulle. An absolute stunner!

7. Anne Hathaway

Anne looked like a delicate rose in bloom in a scarlet draped, asymmetric Marchesa gown. She really stood out and there was no way she’d be left off of this list.


6. Hilary Swank

The 2005 Academy Awards was a night to remember for Hilary, and for all the right reasons! There was quite a stir on the red carpet as her seemingly conservative, Guy Laroche gown revealed a daringly low back. This navy number is undoubtedly one of the most amazing garments seen on the red carpet.

5. Jessica Alba

Jessica Alba dazzled in a glittering gold Versace dress at the 2006 Academy Awards. It was a sophisticated bare back and halterneck that showed off her stunning body.

4. Gwyneth Paltrow

The simple, elegant and high fashion minimalist, white Tom Ford gown and a matching cape that Paltrow wore to the 2012 Oscars was the standout look on the famous red carpet.


3. Jennifer Lawrence

Jennifer Lawrence was the belle of the ball in a Christian Dior gown. The beautiful garment won't be one she'll forget in a hurry as the Oscar-winner actress tripped over the front of her full-skirted dress upon collecting her award in front of the live audience and everyone watching at home. Fashion has a price!

2. Amanda Seyfried

Seyfried’s choice to wear a muted palette Alexander McQueen gown was a winner and with her hair pinned back, gave her a timeless look we absolutely love.

1. Lupita Nyong’o

We had to end with our favourite, a young lady that showed up for Nigeria and for Africa. Nyong’o’s powder blue Prada gown is the stuff legends are made of. The lovely Marilyn Monroe dress flattered her in every way and she matched it with perfect accessories. And, to top it off, she also won the Supporting Actress Oscar and gave hope to aspiring actresses all across Africa.

Don’t miss the red carpet at the 87th Annual Academy Awards. We hope to see more incredible outfits that will also make lists like this in the future. And, let’s not forget what the show is all about, honouring cinematic achievements in the film industry. All the best to the nominees!


See our enticing red carpet predictions for 2015 or discover how to dress like a style icon.