Flashback: Oscars Red Carpet Hits & Misses Ranked

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The Oscars never fail to be the most anticipated award show of the season each year! It’s one of the most glamorous red carpets and stars dress to the nines for the occasion. Throughout the years, we’ve definitely seen our fair share of memorable Oscars’ red carpet moments, but whether they were hits or misses are still up for question. Follow along as we round up and rank all the Oscars red carpet hits and misses from years past.

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72. Hit: Regina King — 2019

Of all the looks at the 2019 Academy Awards, our favorite had to be this white pleated dress worn by Regina King. The look was classy and elegant, but still a little sultry with the thigh-high slit. Her look proved that sometimes simplicity is key when it comes to red carpet fashion.

(Photo by Richard Shotwell/Invision/AP)

71. Miss: Emily Blunt — 2018

Emily Blunt undeniably missed the mark with this powder blue number she wore on the 2018 Oscars red carpet. The chiffon dress featured an outdated looking high-neckline and cap sleeve detailing. This look seemed to age Blunt and looked a little stifling.

Photo by Lionel Hahn/ABACAPRESS.COM

70. Hit: Brie Larson — 2016

Brie Larson stunned at the 2016 Academy Awards where she stepped out wearing a cobalt blue dress with delicate ruffles trailing down the front. This deep jewel tone looked perfect with Larson’s skin tone and the beaded belt brought a touch of glitz to her red carpet ensemble.

EPA/MIKE NELSON

68. Miss: Gemma Chan — 2019

Crazy Rich Asians star Gemma Chan has proved that she has a strong sense of style based on her previous red carpet looks, which is why we were disappointed with this oversized pink number she opted for at the 2019 Oscars. The color looked fabulous on her skin tone, but this dress simply did nothing for her figure and felt like it drowned her.

EPA/ETIENNE LAURENT

67. Hit: Cameron Diaz — 2010

Cameron Diaz looked like a total bombshell at the 2010 Academy Awards where she stepped out wearing this jewel-encrusted golden gown by Oscar De La Renta. The look fit her like a glove and was the epitome of red carpet glitz and glamour.

Source: Shutterstock

66. Miss: Kacey Musgraves — 2019

We were totally shocked by this baby pink look worn by Kacey Musgraves at the 2019 Oscars. It was the definition of foofy and many fans tuning in even compared her look to a loofah! As much as we love and support Kacey Musgraves, this dress simply wasn’t the most flattering.

(Photo by Jordan Strauss/Invision/AP)

65. Hit: Anna Kendrick — 2010

Anna Kendrick looked absolutely gorgeous at the 2010 Academy Awards where she opted for a pale pink dress by Ellie Saab. The look featured subtle pleating in various directions and a sultry off-the-shoulder neckline. We especially love the floral embellishment on the bodice and the pop of lace on the slit.

Emilio Flores/Everett Collection

64. Miss: Charlize Theron — 2019

We have high expectations for Charlize Theron when she hits the red carpet, but we, unfortunately, weren’t thrilled with her choice of dress for the 2019 Oscars. The look didn’t feel properly tailored to her body, especially with the cuffed sleeves.

Photo by Lionel Hahn/ABACAPRESS.COM

63. Hit: Rachel Weisz — 2007

When Rachel Weisz stepped out at the Academy Awards in 2007 she instantly had all eyes on her. The starlet donned a slinky slip dress in a lovely shade of metallic silver. It was sultry, but totally red carpet glamorous, which is why it has stuck in our memory as one of the most memorable Oscars’ looks.

Source: Shutterstock

62. Miss: Emma Stone — 2019

We were definitely disappointed with Emma Stone’s look for the 2019 Oscars. The look was designed by Louis Vuitton and featured a bizarre checkered chocolate and gold print. Many were comparing her look to a waffle, which we can totally see!

(Photo by Jordan Strauss/Invision/AP)

61. Hit: Natalie Portman — 2011

No one has mastered maternity style as well as Natalie Portman. The actress looked absolutely gorgeous at the 2011 Academy Awards where she stepped out wearing this off-the-shoulder violet number by Rodarte. The look flattered her budding baby bump and was the perfect rich jewel-tone to complement her golden complexion.

Photo By: Gregorio T. Binuya/Everett Collection

60. Miss: Anne Hathaway — 2007

No one could forget the dress Anne Hathaway wore to the 2007 Oscars! The shape and style of this dress itself aren’t too bad, but the oversized bow detail along the chest definitely received a lot of backlash from fashion critics. Her look would have been much sleeker and stylish without this distracting detail.

Photo by Hahn-Khayat-Douliery/ABACAUSA.COM

59. Hit: Angelina Jolie — 2012

Angelina Jolie’s leg slit took over the 2012 Oscars red carpet when she stepped out wearing this chic black look by Versace. The velvet dress was glamorous, sultry and an iconic Oscars fashion moment that no one could forget.

Photo By: Dee Cercone/Everett Collection

58. Miss: Emma Stone — 2018

Of all the looks from the 2018 Oscars, we were by far the most let down by Emma Stone’s outfit. Stone made a huge impression at the 2017 Oscar red carpet with her gold column-style dress, which is why we had big expectations for her look the following year. The red and pink blazer combo she opted for seemed quite casual and the colors clashed, which was disappointing. There was also too much silk happening at once and we wish she would have mixed up the textures.

Photo by Lionel Hahn/ABACAPRESS.COM

57. Hit: Naomi Watts — 2013

Naomi Watts stepped out at the 2013 Oscars wearing this gunmetal silver dress that fit her like a glove. We absolutely love the geometric cutout of this look around the neckline, which really made this stand out as a memorable Oscars fashion moment.

Source: Press Association

56. Miss: Jennifer Hudson — 2007

Jennifer Hudson stepped out at the 2007 Oscars wearing a chocolate brown dress with pockets that landed at the top of nearly every worst-dressed list. To make matters worse, she topped the look with a strangely sculpted bolero jacket which clashed and felt over the top.

Photo by Hahn-Khayat-Douliery/ABACAUSA.COM

55. Hit: Cate Blanchett — 2016

Cate Blanchett looked absolutely angelic on the 2016 Oscars red carpet when she stepped out wearing this floral-embellished Armani Prive dress. We absolutely love the unique seafoam green shade of this dress and how much of a statement all the embellishment made.

Source: Press Association

54. Miss: Lady Gaga — 2015

Lady Gaga has made a name for herself over the years for her bold and eccentric sense of style, but her look for the 2015 Oscars just left us totally confused. The dress itself wasn’t too bad and was actually quite pretty with the sculpted shoulders and glittering texture, but the red, rubber glove-like accessory she wore on her hands totally detracted from the dress.

(Photo by Jordan Strauss/Invision/AP)

53. Hit: Emma Stone — 2017

One of Emma Stone’s most memorable fashion moments is when she attended the 2017 Oscars wearing this Givenchy haute couture gown. The dress featured gold Swarovski crystal embroidery on the bodice as well as an ombre crystal fringe on the skirt.

(Photo by Jordan Strauss/Invision/AP)

52. Miss: Jennifer Connelly — 2002

We have to admit we weren’t the biggest fans of the taupe layered dress that Jennifer Connelly wore to the 2002 Academy Awards. The look felt shabby, especially with the raggedy tiers trailing down the skirt. To make matters worse, Connelly topped her look with an extra-long yellow scarf which, unfortunately, detracted from the look even further.

Source: Press Association

51. Hit: Alicia Vikander — 2013

Alicia Vikander absolutely stunned at the 2013 Oscars where she stepped out in this delicate lace gown in a flattering shade of teal blue. The beaded Ellie Saab gown showed off her dainty, petite frame perfectly but was still a little sultry with the mesh paneling.

Source: Shutterstock

50. Miss: Faith Hill — 2002

Faith Hill attended the 2002 Oscars wearing a rainbow dress that will forever be remembered as one of the most disappointing Oscars looks. From the heavy beading to the pastel range of colors, this look definitely felt overwhelming, and ultimately, over the top.

Source: Press Association

49. Hit: Gwyneth Paltrow — 2012

Gwyneth Paltrow was a vision in white at the 2012 Oscars where she stepped out in this crisp and sophisticated dress by Tom Ford. The floor-length cape was the epitome of Hollywood glamour and is definitely an Oscars look that we’ll never forget.

Source: Shutterstock

48. Miss: Bjork — 2001

How could we forget Bjork’s infamous swan dress from the 2001 Oscars? The Icelandic singer donned a feathered frock by Marjan Pejoski with no shame and this eccentric creation has undeniably landed her on many worst dressed lists over the years. We’ve seen tasteful feathers on dresses throughout red carpet history, but never before had we seen a full-blown bird worn as a gown.

Photo By STEWART COOK / Rex Features

47. Hit: Anne Hathaway — 2009

Anne Hathaway stunned at the 2009 Oscars red carpet where she stepped out wearing this form-fitting metallic gown by Giorgio Armani Prive. The slinky number fit her like a glove and brought the red carpet glamour factor with its subtle shimmering texture. This look worn by Anne Hathaway is definitely a red carpet moment we’ll never forget!

Emilio Flores/Everett Collection

46. Miss: Juliette Binoche — 1997

Juliette Binoche stepped out at the 1997 Oscar awards wearing a head-to-toe velvet dress that no one could forget. Unfortunately, the dress felt quite heavy with the dark velvet texture and was a little too vampire-esque for our taste.

Source: Press Association

45. Hit: Nicole Kidman — 2018

Nicole Kidman nailed her 2018 Oscars look when she stepped out wearing this royal blue number designed by Armani Prive. The look featured a plunging sweetheart neckline and an exaggerated bow detail along the hip. Kidman is definitely not shy to take a fashion risk or two, which we love about her, and this particular sophisticated look was undeniably a risk that was well rewarded!

Photo by Jordan Strauss/Invision/AP

44. Miss: Charlize Theron — 2006

Charlize Theron stepped out at the 2006 Oscars wearing a dress designed by Galliano for Dior. Her look was, unfortunately, a little too bold for our liking, especially with the oversized bow detail on the shoulder that was totally distracting.

Source: Press Association

43. Hit: Sandra Bullock — 2018

Sandra Bullock looked striking on the 2018 Oscar’s red carpet while wearing this shimmering Louis Vuitton gown! The custom-made black and silver garment featured a flattering halter neckline and a ruffled detail cascading from the hip. The captivating number was the perfect balance of elegance and edginess.

Photo by Jordan Strauss/Invision/AP

42. Miss: Kate Winslet — 2016

Kate Winslet stepped out at the 2016 Oscars wearing a Ralph Lauren dress that had one major issue — the texture! The dress picked up on camera looking almost latex-like with the glossy finish, which really came across as quite tacky.

Photo By: Elizabeth Goodenough/Everett Collection

41. Hit: Eiza Gonzalez — 2018

Eiza Gonzalez undeniably made head turns on the 2018 Oscars red carpet where she wore this show-stopping canary yellow number! The look featured glamorous cutouts along the sides that showed an appropriate amount of skin without looking tacky. We love that she topped this look with an unconventional red lip for something different and for added drama.

EPA/MIKE NELSON

40. Miss: Dakota Johnson — 2017

Dakota Johnson’s 2017 Oscars dress definitely earned a lot of buzz following the event, but unfortunately not in a positive way. The star hid her fabulous figure among layers of silk and the entire dress seemed outdated and almost as if it belonged in the Victorian era with its ruffled collar, puffy shoulders, and long sleeves. The Gucci gown was overly modest, a strange yellowed shade of champagne and featured a bizarre ruffle detail at her waist that was unflattering.

David Fisher/REX/Shutterstock

39. Hit: Jennifer Garner — 2018

Jennifer Garner stole the show at the 2018 Oscars when she stepped out wearing this eye-catching Atelier Versace number. The brunette beauty rocked a striking cobalt blue dress that featured an asymmetrical neckline and a dramatic cape that trailed elegantly behind her as she walked. This choice of color and cut couldn’t have been more perfect!

Photo by Jordan Strauss/Invision/AP

38. Miss: Salma Hayek — 2018

Of all the looks from the 2018 Oscars, we were the most confused by Salma Hayek’s sequin gown. The obscure look felt quite tacky and juvenile which was disappointing to see on the ever-elegant Hayek. There was purple, glitter, diamonds, and tiers which simply came together to look quite chaotic and questionable.

Source: Abaca Press

37. Hit: Grace Kelly — 1955

Grace Kelly is one of Hollywood’s most elegant icons, but her look from the 1955 Oscars was especially remarkable. The pale ice blue dress designed by Edith Head featured a dainty double strap and a luxurious silk texture that hugged her body perfectly. Suited for the classy woman she is, Kelly wore a pair of sleek white gloves as accessories and delicate pearl earrings. She coiffed her hair into an updo which was topped with romantic rosebuds throughout.

Everett Collection

36. Miss: Jodie Foster — 1989

Jodie Foster definitely dressed to stand out at the Academy Awards in 1989! Although we appreciate the risk, we’re not entirely sure the result was one of her better awards show looks. The sky blue dress definitely hugged her curves in all the right places, but the oversized frills draping from her hips seemed tacky rather than glamorous. It overwhelmed her frame and seemed to distract from her beauty rather than complement it.

Source: Everett Collection

35. Hit: Audrey Hepburn — 1964

Audrey Hepburn is another Hollywood icon that looked absolutely striking whenever she stepped onto the red carpet! Hepburn’s floral look from the 1964 Academy Awards was definitely one of her most memorable. The Givenchy number was the epitome of old Hollywood glam with its A-line shape and couture detailing. The dress flattered her tiny figure and the belt-detailing around her waist further emphasized her petite frame.

Source: Everett Collection

34. Miss: Sophia Loren — 2009

Sophia Loren is a Hollywood legend, but unfortunately, the dress she wore to the 2009 Oscars missed the mark. The frothy golden number featured oversized ruffles and frill in all the wrong places in addition to strange sparkly straps and sheer mesh sleeves.

Dee Cercone/Everett Collection

33. Hit: Julia Roberts — 2001

Julia Roberts’ Valentino number from 2001 was one of her most breathtaking looks to date! The vintage gown featured a dainty halter neckline and a sleek, body-hugging shape that definitely stole the show. The vintage number was fitted and sophisticated but still romantic, especially with the glamorous train that cascaded behind her as she walked. The smooth updo definitely softened the entire look and added a touch of old Hollywood glamour.

Source: Shutterstock

32. Miss: Hilary Swank — 2003

Hilary Swank has had a couple of killer red carpet moments, but unfortunately, this frothy pink dress wasn’t one of them. The look was definitely elegant and whimsical, but many fashion critics likened it as a dress that would be more suited for prom or a sweet 16 birthday party than the Academy Awards. We appreciate the dramatic effect of the sweeping skirt, but the tulle and ombre pink effect definitely came across a little too juvenile.

ABC/Courtesy Everett Collection

31. Hit: Jennifer Lopez — 2003

Jennifer Lopez stepped out in 2003 wearing a mint green Valentino number that was the perfect color selection to flatter her bronzed complexion. The gown featured a stunning one-shoulder neckline that had soft, sparkling embellishment around the edges. The look was definitely one of Lopez’s best of all time and although it was relatively clean and simple, it definitely made a lasting impression for years to come following the event.

Source: Shutterstock

30. Miss: Jennifer Lopez — 2010

Jennifer Lopez is typically a red carpet all-star, which is why we were all the more disappointed when she stepped out in 2010 wearing this dramatic Armani Prive number. We’re used to J.Lo’s alluring and sleek red carpet gowns, and this ruffled, foofy number seemed to drown her hourglass figure. With a body as enviable as Jennifer Lopez, it’s a shame that she decided to wear a dress with such exaggerated layering and ruffles.

Source: Shutterstock

29. Hit: Hilary Swank — 2005

Hilary Swank’s Guy Laroche navy number from the 2005 Oscars made one of the biggest fashion statements in red carpet history! At the time, a completely backless look like this was revolutionary, but it went on to inspire generations of designers for years to come. The stunning sapphire number proves that it doesn’t take embellishment or glitter to make a fashion statement and that often the cut of the dress is what makes the biggest impact.

Photo: ABC/Craig Sjodin/Courtesy Everett Collection.

28. Miss: Diane Keaton — 2004

Diane Keaton has always had an out-of-the-box sense of fashion, but this particular look from the 2004 Oscar’s red carpet was definitely one of her most bizarre. The tuxedo look consisted of a long cutaway jacket which she paired with a striped vest, pants and polka dot tie. For accessories, Keaton opted for a top hat, leather gloves, and strange tinted glasses. We love a strong tuxedo look on the red carpet, but unfortunately, Keaton’s came across messy and distracting.

Source: Shutterstock

27. Hit: Reese Witherspoon — 2006

Reese Witherspoon looked absolutely dreamy on the 2006 red carpet when she stepped out wearing a vintage 1955 Dior number. Rumor has it that Reese discovered the hidden gem tucked away in a Paris vintage boutique! She initially had trouble convincing the shop owner to part with it because, according to her, it had once belonged to royalty. Clearly, Reese won in the end and the result was an absolutely enchanting red carpet fashion moment.

26. Miss: Tilda Swinton — 2008

Tilda Swinton is one of the most influential style icons in Hollywood, but unfortunately, her 2003 look for the Academy Awards was not one of her best. The Lanvin dress featured a high-shine velvet texture that looked cheap rather than luxurious and sleek. The gown seemed to cling to all the wrong places of her body and the asymmetrical one shoulder long-sleeve seemed to drown her slender frame rather than flatter it.

David Longendyke/Everett Collection

25. Hit: Sandra Bullock — 2010

Sandra Bullock absolutely dazzled back in 2010 when she took to the Oscars’ red carpet wearing this glittering champagne number. The Marchesa garment featured a sheer bodice that had strategically placed embellishment and beading throughout. The gown flourished into a full glitter skirt that hugged her figure and trailed gracefully behind her as she walked. Bullock is hardly one to opt for sparkle on the red carpet which made this look all the more striking and notable.

Photo by BDG / Rex Features

24. Miss: Uma Thurman — 2004

Uma Thurman’s 2004 Oscars’ look was definitely one of the most questionable in red carpet history. The theatrical, costume-like look seemed to be something straight of a film rather than a respectable dress worn to an event that honors film. The look consisted of lace, a blue sash and heavy metallic detailing which did not pair well together.

Source: Shutterstock

23. Hit: Mila Kunis — 2011

Mila Kunis’ 2011 Academy Awards look definitely generated quite a bit of buzz! The eye-catching lavender number was designed by Ellie Saab and featured a chiffon texture, tiered lace detailing and a flattering ribbon which tied around the waist. We absolutely love the whimsical, romantic feel of this feminine gown and the soft purple color was striking against Mila’s dark features and hair.

Jef Hernandez/Everett Collection

22. Miss: Celine Dion — 1999

Celine Dion’s 1999 Oscars’ look was definitely one of the most confusing of all time! Dion is known for her risky fashion looks, and often they are rewarded, but that was unfortunately not the case with this silk outfit. She broke fashion barriers by wearing her crisp tuxedo backward and pairing it with an oversized top hat. We love Celine’s tendency to step out of the box with her fashion, but this look was admittedly a little too bizarre to be praised.

Photo By Rex Features

21. Hit: Lupita Nyong’o — 2014

Lupita Nyong’o was a red carpet newbie when she stepped out at the Oscars back in 2014! She clearly knew how to make an impact and opted for a powder blue Prada gown that looked absolutely stunning on her. At the time, Nyong’o shared that she picked the color specifically because it reminded her of her home, Nairobi. The pleated gown featured an elegant drop-style neckline and a full skirt which was completely glamorous, especially when topped with the sparkling diamond headband.

Photo By: Gregorio Binuya/Everett Collection

20. Miss: Sarah Jessica Parker

Sarah Jessica Parker is known for her bold and beautiful red carpet looks. The actress wore a champagne-colored gown from the Chanel Couture Spring 2010 runway to the 82nd Annual Academy Awards and while the dress is unique, it does not flatter the Sexy and the City star’s petite figure and seems to drown her.

19. Hit: Taraji P. Henson — 2017

Taraji P. Henson turned heads when she stepped onto the 2017 Academy Awards red carpet wearing this luxurious velvet number. The Alberta Ferretti design featured an elegant off-the-shoulder neckline, which she topped with a chunky diamond necklace for added glamour. The cut of the dress was relatively simple, but the combination of the rich velvet with the thick diamonds was a display of Hollywood glitz at its finest.

Photo by VG/SilverHub/REX/Shutterstock

18. Miss: Jennifer Garner

The plum coloring on this ruffled Gucci gown is flattering on Jennifer Garner and, if you aren’t considering the back of the dress, the front on its own is quite nice. The only problem is the mass of plumage-like ruffles cascading down the back. The back-detailing was distracting and we would have much preferred if she had opted for something a little more simple with less embellishment.

17. Hit: Gwyneth Paltrow – 1999

At the 1999 Academy Awards, Gwyneth Paltrow showed up wearing a pink taffeta Ralph Lauren gown, which featured a V-shaped neckline and a voluminous skirt. Although some people criticized the dress because it wasn’t properly tailored, overall, it has been remembered as one of the greatest dresses ever worn on the Oscars’ red carpet and Paltrow was credited for bringing pink back in style.

16. Miss: Anne Hathaway

Anne Hathaway opted to wear a pale pink Prada dress for the 85th Annual Academy Awards after she found out Amanda Seyfried was going to be wearing something remarkably similar to the Valentino gown she had originally selected. Unfortunately, the color and the fit of the dress were anything but flattering and the dress itself was quite underwhelming and dull. We understand the controversy and inconvenience of the last minute switch, but Hathaway definitely fell short of our fashion expectations with this look.

15. Hit: Priyanka Chopra — 2017

No one could possibly forget Priyanka Chopra’s statement look from the 2017 Oscars’ red carpet! The crisp column-style dress was designed by Ralph & Russo and featured a geometric pattern throughout and a sharp square-shaped neckline. The look was a little avant-garde but still flattering and totally elegant. She topped the look with sparkling diamonds and sleeked her straight hair behind her ears.

Elizabeth Goodenough/Everett Collection

14. Miss: Halle Berry

Halle Berry wore a plunging metallic Versace gown to the 85th annual Academy Awards and while some may argue that the dress looks sexy, we think it looks a bit too busy and doesn’t flatter her amazing curves. It simply seemed to blend in with the rest of the dark, metallic dresses on the red carpet and hasn’t stood out in our memory as particularly memorable.

13. Hit: Halle Berry – 2002

On the other hand, Berry wore an Elie Saab dress to the 2002 Academy Awards that was definitely one of her most memorable looks ever. The top of the dress was made of mesh with some strategic embroidering over the chest with a maroon-colored satin skirt. It’s considered one of the greatest Oscar dresses ever because it was edgy and revealing, but at the same time left a lot to the imagination.

Everett Collection

12. Miss: Charlize Theron

Charlize Theron arrived at the 82nd Annual Academy Awards wearing the pink version of Lindsay Ellingson’s Dior Spring 2010 Couture gown. The details on the bust were a little too theatrical feeling and the satin texture seemed to wrinkle which didn’t feel the most elevated.

11. Hit: Michelle Williams – 2006

Michelle Williams didn’t win the Oscar for Best Supporting Actress in this saffron yellow Vera Wang gown, but she did receive critical acclaim for her bold fashion choice. While the color was initially panned, it became one of the hottest hues in Hollywood. The style of the dress combined with Williams’ bright red lips and wispy hair made her look as if she came out of an old Hollywood film.

Rex Feature Ltd.

10. Miss: Angelina Jolie

Angelina Jolie is one of the most attractive women in Hollywood; however, the black long-sleeved Versace gown that she wore to the 72nd Annual Academy Awards didn’t do her justice. The dress, combined with the heavy makeup and jet black hair felt a little heavy on the gorgeous actress. We would have much preferred something a little more whimsical and light to celebrate her win rather than this dark, bland look.

9. Hit: Nicole Kidman – 2007

Nicole Kidman has attended so many Academy Award ceremonies over the years and she almost always lands on the best-dressed lists; however, there is one dress, in particular, that is by far the most memorable. In 2007, she wore a red eye-catching Balenciaga gown with a dramatic bow at the neck. Although she initially received a lot of flack for sporting a bow bigger than her head, all agreed that the dress was beautiful.

Rex Feature Ltd.

8. Miss: Kate Hudson

Kate Hudson is the kind of actress who typically lights up the carpet with her California girl style and her youthful exuberance. Unfortunately, the Stella McCartney dress that she wore to the 73rd Annual Academy Awards, paired with a not-so-sophisticated curly updo, seemed to age the young actress and wasn’t the most flattering.

7. Hit: Penelope Cruz – 2007

Penelope Cruz wore a stunning dusty pink feathered Versace number to the 2007 Academy Awards. The strapless gown flattered her hourglass figure flawlessly with its fitted bodice and long feathery train. Given the couture details on the dress, we’re not at all surprised that it is considered one of the most beautiful and iconic Oscar dresses of all time.

6. Miss: Jessica Biel

Jessica Biel has one of the most beautiful faces in Hollywood with a perfect figure to boot, so her decision to wear this ill-fitted cream-colored Prada gown with oversized draping wasn’t the most well-received. In recent years Biel has proven herself to be one of the most well-dressed women to watch on the red carpet, but that’s not to say her past didn’t come with a few misses, like this silky number!

5. Hit: Jessica Chastain – 2012

On the red carpet, Jessica Chastain’s fashion has been a hit or miss, but at the 2012 Oscars, she hit it out of the ballpark with this daring Alexander McQueen number. She looked absolutely regal in the black strapless gown, which featured a silk organza corset and gold beaded embroidery. This was definitely one of the more memorable of her gowns and it featured just the right amount of embellishment to be glamorous yet still tasteful.

4. Miss: Gwyneth Paltrow

Style queen, Gwyneth Paltrow, wore this goth Alexander McQueen dress to the 74th Annual Academy Awards and, looking back on it, she sees some major issues with the dress! “There were a few issues; I still love the dress itself but I should have worn a bra and I should have just had simple beachy hair and less makeup. Then, it would have worked as I wanted it to – a little bit of punk at the Oscars,” she said.

3. Hit: Amy Adams – 2013

Amy Adams looked angelic at the 2013 Academy Awards in this silver strapless Oscar de la Renta gown. The look featured a feathery tulle skirt and a flattering sweetheart bodice that ruched across the front. This dress was definitely memorable because it was sophisticated and sharp yet still made a statement.

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2. Miss: Sandra Bullock

Sandra Bullock can be hit-or-miss on the red carpet but this black and white Marchesa dress from the 84th Annual Academy Awards was admittedly disappointing. The actress has an amazing figure and with the lack of tailoring, you can’t see her amazing curves at all. The top looks too big and the bottom looks like it belongs to another dress altogether. Bullock has had a handful of awe-worthy red carpet moments, but unfortunately, this look was definitely not one of them.

1. Hit: Jennifer Lawrence – 2013

Jennifer Lawrence’s pale pink Christian Dior Couture gown that she wore to the 2013 Oscars was definitely the most dramatic dress choice at the event. With its strapless silhouette and ultra-voluminous skirt, she looked like she came straight from a Disney movie where she played the princess. It’s no wonder her outfit was so memorable – she was styled by none other than celebrity stylist Rachel Zoe!

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