100 Best Dresses of the Decade

InStyle.com

Dec 15, 2009 @ 11:31 am

From barely-there figure-flaunters to sophisticated sheaths, the last 10 years have been great for gowns. Take a walk down memory lane (via the red carpet!) with InStyle fashion director Hal Rubenstein.

RELATED VIDEO: The Most Naked Dresses of All Time

1 of 100 SGranitz/WireImage

Kate Hudson in Versace

WHERE 75th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "It had a level of extravagance that just had you gasping. The combination of her golden skin, golden hair and the yards of gold lace-I was stunned."

-Hal Rubenstein, Fashion Director

2 of 100 Mario Anzuoni/Landov

Anne Hathaway in Armani Prive

WHERE 81st Annual Academy Awards in Los Angeles
WHY WE LOVE IT "The huge, iridescent paillettes came down at a diagonal and created a great mermaid effect. This dress almost matched her skin tone and was like a burst of light underneath her."

3 of 100 Rob Beccaris/WireImage

Charlize Theron in Vera Wang

WHERE 72nd Annual Academy Awards in Los Angeles
WHY WE LOVE IT "Vera understands real, sexy, old-fashioned, 'knock 'em dead' glamour. The color is just great and, of course, the diamonds are perfectly placed. It’s Old Hollywood without looking old."

4 of 100 Steve Granitz/WireImage

Eva Mendes in Dior

WHERE 68th Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "This look has one moment of extravagance and shows that proportion is everything. If that wonderful fold at her hip was two inches wider or longer it might have failed-but it was so right. The Van Cleef & Arpels necklace is a spectacular complement."

5 of 100 Steve Granitz/WireImage

Penelope Cruz in Atelier Versace

WHERE 81st Annual Academy Awards in Los Angeles
WHY WE LOVE IT "Three things: A refined moment with her hair and makeup, a va-va-va-voom moment where the dress fits so close to her body and a big glamour moment with the intricate train that goes on forever."

6 of 100 Paul Smith/Featureflash/Retna

Gwen Stefani in Valentino

WHERE 61st Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT “Here’s the rocker chick wearing the most unlikely dress of the night. It’s all about going against the grain and throwing people off.”

7 of 100 Evan Agostini/Getty Images

Jessica Alba in Dolce & Gabbana

WHERE 58th International Cannes Film Festival in Cannes, France
WHY WE LOVE IT "The movement of the fabric against her great body is sexy and, as sparkly as the dress is, there’s something very withholding about it."

8 of 100 Steve Granitz/WireImage

Kate Winslet in Atelier YSL

WHERE 81st Annual Academy Awards in Los Angeles
WHY WE LOVE IT "This dress shows the sexiness of a real woman who makes no apologies for her curves."

9 of 100 Fernando Allende/CelebrityPhoto

Sarah Jessica Parker in Chanel

WHERE 55th Annual Emmy Awards in Los Angeles
WHY WE LOVE IT "There's something so happy about this dress. Those fabulous, weightless layers of organza-it’s like cotton candy or a pink meringue souffle. They didn’t bother with hair and makeup because the dress was such an eye-popper."

10 of 100 Dave Allocca/Startraks Photo

Drew Barrymore in Alberta Ferretti

WHERE Grey Gardens premiere in New York City
WHY WE LOVE IT "Drew was channeling a femme fatale with the twenties hair and bee-stung lips. It had that unabashed boudoir feel that Alberta does so well."

11 of 100 Gregg DeGuire/WireImage

Joy Bryant in Donna Karan

WHERE The Skeleton Key premiere in Los Angeles
WHY WE LOVE IT "Everything comes dead center to the waist and starbursts out from there. It’s about a woman being proud of her curves."

12 of 100 Frazer Harrison/Getty

Reese Witherspoon in Nina Ricci

WHERE 65th Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "This was Reese's first moment out after her split with Ryan Philippe: Strapless, short, yellow, unadorned and showing her body. I love the unexpectedness of it. It was a brilliant strategy and it really worked."

13 of 100 Fitzroy Barrett/Globe Photos

Jennifer Lopez in Versace

WHERE 42nd Annual Grammy Awards in Los Angeles
WHY WE LOVE IT "Her bravado is unbelievable. It’s funny because you want to tear the dress apart, yet when she showed up you couldn’t take your eyes off her."

14 of 100 Dave Hogan/Getty Images

Cate Blanchett in Prada

WHERE BAFTA Awards in London
WHY WE LOVE IT "Prada took a classic flash of glamour and added the little lingerie moments against a quiet T-strap shoe."

Sarah Jessica Parker in Richard Tyler, 2000

15 of 100 Jim Smeal/WireImage

SJP in Richard Tyler

WHERE 57th Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "It was layer upon layer of beaded tulle and was this wonderful blush color that perfectly matched her skin tone."

16 of 100 Frank Micelotta/Getty Images

Uma Thurman in Jean Paul Gaultier

WHERE 53rd Annual Cannes Film Festival in Cannes, France
WHY WE LOVE IT "There’s something very calm about the dress in the sense that it’s not about the usual Hollywood drama. It’s as if you took old scarves and sewed them all together."

17 of 100 Jeffrey Mayer/Wireimage

Halle Berry in Valentino

WHERE 57th Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "The red stones jump out like a shower of little roses accenting the smallness of Halle’s waist. They were like two fires burning from the middle and bottom of the dress."

18 of 100 Steve Granitz/WireImage

Charlize Theron in Narciso Rodriguez

WHERE El Captain Theatre in Los Angeles
WHY WE LOVE IT "She looked like a glamorous savage. The torn beading and asymmetrical hem gave it an element of sophisticated grunge."

19 of 100 KMazur/WireImage

Penelope Cruz in Ralph Lauren

WHERE 72nd Annual Academy Awards in Los Angeles
WHY WE LOVE IT "Ralph’s clothes never upstage the woman wearing them. He took his classic shape, pulled it off the shoulder and added an incredibly sheer shawl."

20 of 100 Evan Agostini/ImageDirect/Getty Images

Demi Moore in Donna Karan

WHERE Costume Institute Gala in New York City
WHY WE LOVE IT "There’s almost a deconstructed extravagance or luxury in this dress. The one shoulder gives it a goddess quality."

21 of 100 Jon Furniss/WireImage

Kate Beckinsale in Givenchy

WHERE Pearl Harbor premiere in London
WHY WE LOVE IT "It has this perverse, milkmaid-hits-the-red-carpet quality that I love. Also, the belt was made of this unbelievably thick, saddle-like leather."

22 of 100 SGranitz/WireImage

Michael Michele in Hermes

WHERE Ali premiere in Los Angeles
WHY WE LOVE IT "You can imagine someone wearing it on a red carpet or while walking around barefoot at home. I think any woman who bought this dress would wear it forever."

23 of 100 Fitzroy Barrett/Globe Photos

Julianna Margulies in Oscar De La Renta

WHERE 56th Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "This was a true fairy-tale princess gown. It looks as if somebody captured the heavens and wrapped it into a dress."

24 of 100 Dave Hogan/Getty Images

Nicole Kidman in Jean Paul Gaultier

WHERE Moulin Rouge premiere in London
WHY WE LOVE IT "I like dresses that cover up everything but one asset. In this case, it’s her legs. It’s just so smart and brilliantly accessorized."

25 of 100 Theo Wargo/WireImage

Jennifer Lopez in Alexander McQueen

WHERE MTV Video Music Awards in New York City
WHY WE LOVE IT "This was very 19th century swashbuckler. The big heavy locket and the curly hair make it a great look from top to bottom."

26 of 100 Dave Hogan/Getty Images

Jennifer Connelly in Vivienne Westwood

WHERE BAFTA Awards in London
WHY WE LOVE IT "The dress looks classic but there’s a deliberate off-centeredness. This little twist makes the dress far more interesting and idiosyncratic."

27 of 100 Gilbert Flores/Celebrity Photo

Heather Locklear in Michael Kors

WHERE 59th Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "The beige and turquoise highlighted her tan while the diamonds and rhinestones lit up her hair and eyes. There’s something cheeky about throwing so much onto something little."

28 of 100 Gilbert Flores/Celebrity Photo

Oprah Winfrey in Bradley Bayou

WHERE 54th Annual Emmy Awards in Los Angeles
WHY WE LOVE IT "There’s something queenly and regal about the dress just as there’s something very regal about Oprah. She’s like the Czarina of the world."

29 of 100 SGranitz/WireImage

Halle Berry in Collette Dinnigan

WHERE Die Another Day premiere in Los Angeles
WHY WE LOVE IT "There's something about the combination of the Peter Pan haircut, the uneven hem and the sheerness of the beading. She looks like a fabulous sprite!"

30 of 100 SGranitz/WireImage

Kate Beckinsale in Gucci

WHERE 8th Annual Screen Actors Guild Awards in Los Angeles
WHY WE LOVE IT "It was this weird mix of virginal and sensual. When she moved it was like it became a fabulous night gown."

31 of 100 KMazur/WireImage

Kate Hudson in Valentino

WHERE 60th Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "This is one of my favorite Valentino dresses ever. It’s not what you’d expect on a red carpet because it’s so riveting and untamed. The vibrant colors evoked Kate’s free spirit."

32 of 100 KMazur/WireImage

Gwen Stefani in Vivienne Westwood

WHERE 45th Annual Grammy Awards in New York City
WHY WE LOVE IT "This is just too cool for school. It's very strong and dramatic with the white cape that fit perfectly. She was definitely having a Marilyn moment."

33 of 100 Carmen Valdes/Ron Galella/WireImage

Selma Blair in Behnaz Sarafpour

WHERE Costume Institute Gala in New York City
WHY WE LOVE IT "There’s something very modern fairy-tale princess about this dress that’s simple and reserved. Selma has that natural minimalist reserve about her too."

34 of 100 Jean-Paul Aussenard/WireImage

Renee Zellweger in Carolina Herrera

WHERE 55th Annual Directors Guild of America Awards in Los Angeles
WHY WE LOVE IT "The sheer panel in the front was teasing while the red belt gave it an old-fashioned elegant structure. It’s a very interesting juxtaposition."

35 of 100 Gregg DeGuire/WireImage

Victoria Beckham in Dolce & Gabbana

WHERE MTV Movie Awards in Los Angeles
WHY WE LOVE IT "This entire dress is a corset from top to bottom. It’s like the greatest undergarment you’ve ever seen."

36 of 100 SGranitz/WireImage

Diane Lane in Oscar De La Renta

WHERE 75th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "I like the idea of the fringes and that wide wrap that comes right across the arms. It’s incredibly flattering on a woman."

37 of 100 Mirek Towski/Filmmagic

Kate Hudson in Jean Paul Gaultier

WHERE How to Lose a Guy in 10 Days premiere in Los Angeles
WHY WE LOVE IT "Sometimes it’s all about the right placement of beading and gathering. This had a very Charleston moment to it—it has that sort of flapper insouciance."

38 of 100 eter Kramer/Getty Images

Scarlett Johansson in Calvin Klein

WHERE Costume Institute Gala in New York City
WHY WE LOVE IT "It has the neckline that someone in the court of Versailles would've worn- pushed up just enough to make it irresistible."

39 of 100 Rabbani and Solimene Photography/WireImage

Natalie Portman in Stella McCartney

WHERE Costume Institute Gala in New York City
WHY WE LOVE IT "The dress is a whole series of V’s and triangles on the neck piece, daecolletage and hem that create a perfect sense of balance."

40 of 100 SGranitz/WireImage

Julia Roberts in Armani

WHERE 76th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "Julia is more likely to show up on the red carpet in a tuxedo. Seeing her dressed this way was a very Hollywood moment."

41 of 100 Hahn-Khayat-Nebinger/Abaca

Nicole Kidman in Chanel

WHERE 76th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "There’s something completely weightless about this dress. It looks as if it just floated down and landed on her. It's like whipped cream!"

42 of 100 Jeffrey Mayer/WireImage

Kelly Rowland in Dolce & Gabbana

WHERE 18th Annual Soul Train Music Awards in Los Angeles
WHY WE LOVE IT "I've always envisioned that at the heart of Dolce & Gabbana there is a hot Sicilian woman. This is the Dolce & Gabbana dress."

43 of 100 Mark J. Terrill/AP Photo

Jennifer Lopez in Michael Kors

WHERE 61st Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "The crisscross accents her chest and the belt accents her waist. Kors picked a summer-squash orange to play off Jennifer’s golden skin tone."

44 of 100 Gregg DeGuire/WireImage

Thandie Newton in Miu Miu

WHERE The Chronicles Of Riddick premiere in Los Angeles
WHY WE LOVE IT "This dress was about pure proportion. There’s a great balance in the way the dress starts wider at the top and then becomes wider at the bottom."

45 of 100 Gilbert Flores/Celebrity Photo

Kristen Davis in Prada

WHERE 61st Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "This almost had the look of a dress turned inside out. It has a boudoir effect that makes it sexy without being revealing."

46 of 100 KMazur/WireImage

Sheryl Crow in Narsico Rodriguez

WHERE 32nd Annual American Music Awards in Los Angeles
WHY WE LOVE IT "Narciso is so brilliant at understanding fitting. His dresses take on a transformational sorcery that make every woman’s body look their best."

47 of 100 KMazur/WireImage

Gwen Stefani in Vivienne Westwood

WHERE Billboard Music Awards in Las Vegas
WHY WE LOVE IT "There is something ramshackle and grungy about it and yet at the same time it’s so 'I want to party.'"

48 of 100 Steve Granitz/WireImage

Jennifer Garner in Valentino

WHERE 76th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "This is probably the most glamorous Jennifer has ever been on the carpet. The diagonal going across the bodice is incredibly fitted."

49 of 100 SGranitz/WireImage

Kate Bosworth in Louis Vuitton

WHERE The Louis Vuitton United Cancer Front Gala in Los Angeles
WHY WE LOVE IT "It was a very unexpected collection for Vuitton. It’s a modernizing of the old fashioned sense of femininity."

50 of 100 Fernando Allende/Celebrity Photo

Bridget Moynahan in Narciso Rodriguez

WHERE I, Robot premiere in Los Angeles
WHY WE LOVE IT "Narciso is a romantic minimalist. He took a pared down shape and used embroidery to give it great panache. This look is almost urban romantic."

51 of 100 Barry Talesnick/IPOL/GLOBE PHOTOS

Kelly Ripa in Oscar De La Renta

WHERE American Image Awards in New York City
WHY WE LOVE IT "This is Oscar at his prettiest. The little drop waist with the big full skirt-it’s like a variation on a young girl’s party dress."

52 of 100 Dave M. Benett/Getty Images

Ellen Pompeo in Prada, 2004

WHERE Prada store opening in Los Angeles
WHY WE LOVE IT "The fabric had a beautiful movement. You could actually see the intricacies of the hand painting."

53 of 100 SGranitz/WireImage

Hilary Swank in Guy Laroche

WHERE 77th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "This was a really smart move on Hilary’s part. There are few things sexier than a dress with a very high front and a low back. It’s a deliberate attention-getter."

54 of 100 Tim Whitby/WireImage

Kate Hudson in Roberto Cavalli

WHERE The Skeleton Key premiere in London
WHY WE LOVE IT "The slightest sway made the whole dress vibrate with light. It was incredible on the red carpet because it was reflecting and splashing light all over the place."

55 of 100 Carlo Allegri/Getty Images

Gwyneth Paltrow in Stella McCartney

WHERE 77th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "Between the train and Stella’s simple tailoring this dress is incredibly glamorous."

56 of 100 Carlo Allegri/Getty Images

Salma Hayek in Prada

WHERE 77th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "There’s something about this dress that’s so siren-like and very Latin. A woman would go out to dance the cha-cha wearing this."

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Eve in Louis Vuitton

WHERE Louis Vuitton Boutique in Paris, France
WHY WE LOVE IT "This dress just screams innocence with the white eyelet lace plus the peep-toes. It beautifully plays against type."

Kristen Scott Thomas in Yves Saint Laurent, 2005

58 of 100 Badi-Ftw-Sam/Starface/Retna

Kristen Scott Thomas in YSL

WHERE 58th Annual Cannes Film Festival in Cannes, France
WHY WE LOVE IT "She looked like a knockout yet there’s a certain level of reserve to the dress. You could wear it in a 19th century costume drama."

59 of 100 Jason Merritt/FilmMagic

Scarlett Johansson in Roland Mouret

WHERE 62nd Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "This dress is all about the bodice. It has a very '50s movie star, Lana Turner feel."

60 of 100 George Pimentel/WireImage

Sienna Miller in Dior

WHERE Venice Film Festival in Venice
WHY WE LOVE IT "This was a perfect example of how a beautifully draped dress should move. I think every woman in the world would look good in this dress."

61 of 100 Carlo Allegri/Getty Images

Hilary Swank in Calvin Klein

WHERE 62nd Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "The square neckline is like a picture frame while the darting and bodice pushes everything up. I love the strong bronze color against her skin."

Halle Berry in Diane Von Furstenberg, 2006

62 of 100 Dave Allocca/Startraks

Halle Berry in DvF

WHERE On the USS Kearsager to kick off Fleet Week in New York City
WHY WE LOVE IT "It looks fresh, simple and happy. I can’t imagine a woman putting this dress on and not being in a good mood."

63 of 100 Frazer Harrison/Getty Images

Amy Adams in Carolina Herrera

WHERE 78th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "To pick chocolate brown for your first red carpet is very unconventional but it has these wonderful ribbons that framed her body beautifully."

64 of 100 Evan Agostini/Getty Images

Sienna Miller in Burberry

WHERE Costume Institute Gala in New York City
WHY WE LOVE IT "It looks like a shower of gold coins. It’s the personification of retro, cool and English."

65 of 100 Kevin Mazur/WireImage

Kyra Sedgwick in Bottega Veneta

WHERE 64th Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT “On a night where everyone else would be wearing glitter, there’s something very reserved and almost contrary about this dress."

66 of 100 Frank Micelotta/Getty Images

Nicole Kidman in Balenciaga

WHERE 78th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "The incredible ornate beading gives it a romantic feel yet the dress itself is very tightly wound. I love the juxtaposition."

67 of 100 L. Cohen/WireImage

Maria Bello in Donna Karan

WHERE 5th Annual Awards Season Diamond Fashion Show in Los Angeles
WHY WE LOVE IT "It’s such a happy yellow without being gooey. It’s a lot more intricate and sophisticated than it looks at first glance."

68 of 100 George Pimentel/WireImage

Anne Hathaway in Marc Jacobs

WHERE 63rd Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "It’s as if he stole the stars from the sky for this dress. It’s a clear, summer night blue and is just completely garnered with stars."

69 of 100 George Pimentel/WireImage

Joy Bryant in Ralph Lauren

WHERE 31st Annual Toronto International Film Festival
WHY WE LOVE IT "This shows the quiet luxury of a cashmere dress. There’s so much hidden it makes you want to know the woman more."

70 of 100 Stuart Atkins/Rex USA

Keira Knightley in Gucci

WHERE Pirates of the Caribbean: Dead Man's Chest premiere in London
WHY WE LOVE IT "She looked like a siren from the golden age of Hollywood. The whole thing draped so beautifully."

71 of 100 Henry Lamb/Photowire/BEImages

Sienna Miller in Marchesa

WHERE Marchesa's Bergdorf Goodman Anniversary Dinner in New York City
WHY WE LOVE IT "There’s something very neat about the dress. The design is so feminine and light-hearted that it looks more innocent than it is."

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Natalie Portman in Lanvin

WHERE Lower Manhattan Cultural Council's Annual Spring Benefit in New York City
WHY WE LOVE IT "It’s a perfect choice for a young actress who’s transitioning. It’s young but still very urban."

73 of 100 Dan MacMedan/WireImage

Rachel Weisz in Vera Wang

WHERE 79th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "This may have been one of the most beautiful necklines I have ever seen. It’s strapless but it swoops."

74 of 100 George Pimentel/WireImage

Ellen Pompeo in Versace

WHERE 64th Annual Golden Globe Awards in Los Angeles
WHY WE LOVE IT "It looks like a dress that you’d wear to a New Year's Eve party on the Starship Enterprise. I love the futurism."

75 of 100 Paul Drinkwater/NBCU Photo Bank

Helen Mirren in Alexander McQueen

WHERE The Tonight Show with Jay Leno in New York City
WHY WE LOVE IT "You see just enough of her arms, legs and neck. We all know there's aging gracefully-this is aging beautifully."

76 of 100 Jamie McCarthy/WireImage

Sandra Bullock in Alberta Ferretti

WHERE Costume Institute Gala in New York City
WHY WE LOVE IT "We don’t always think of Sandra as a girlie girl. Alberta’s unabashed femininity works for her and softens her in a beautiful way."

77 of 100 Dimitrios Kambouris/WireImage

Drew Barrymore in Donna Karan

WHERE Music and Lyrics premiere in New York City
WHY WE LOVE IT "There's such a womanly air to this look with the beautiful draping and the complement of that huge stone necklace. The combination of the two gave her an elegance that I’d never seen in her before."

78 of 100 Frank Micelotta/Getty Images

Katie Holmes in Lanvin

WHERE 13th Annual Critics' Choice Awards in Los Angeles
WHY WE LOVE IT "I love the grazing yet sculptural quality of the dress and the fact that it’s not the standard, bodice-hugging chiffon. It’s a modernized Grecian gown."

79 of 100 Steve Granitz/WireImage

Cate Blanchett in Armani Prive

WHERE 80th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "It's tight, dense and drenched in these wonderful gunmetal crystals. It’s the intensity of that dark sparkle and the sheer density of the dress that made it so great."

80 of 100 Jon Kopaloff/FilmMagic

Kate Bosworth in Jil Sander

WHERE The 11th Hour premiere in Los Angeles
WHY WE LOVE IT "Simple clothes are the hardest to pull off. There’s a beautiful sort of pristine quality to the dress and I love the way the top of it folds."

81 of 100 Steve Granitz/WireImage

Rihanna in Gucci

WHERE Nickelodeon's 20th Annual Kids' Choice Awards in Los Angeles
WHY WE LOVE IT "It's young and cute yet it doesn’t look childlike. A bold graphic is a hard thing to pull off."

Cameron Diaz, Rachel Zoe, Dior by John Galliano, Dior, Galliano, Fred Leighton, stylist, celebrity style

82 of 100 Gilbert Flores/Celebrity

Cameron Diaz in Dior Couture

WHERE Costume Institute Gala in New York City
WHY WE LOVE IT "The huge turquoise stone necklace with this rollercoaster tiered dress that tumbles all over the place-she jumped in with both feet and instead of getting wet, she made a big splash."

83 of 100 Steve Granitz/WireImage

Penelope Cruz in Chanel

WHERE 80th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "She has a wonderful sense of balance. It's a big dramatic gown with a sort of frilliness in the middle."

84 of 100 Steve Granitz/WireImage

Marion Cotillard in Jean Paul Gaultier

WHERE 80th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "This was like Bottecelli’s 'The Birth of Venus.' It was a great introduction for Cotillard. No one is going to repeat this dress."

85 of 100 Bryan Bedder/Getty Images

Maggie Gyllenhaal in Dries Van Noten

WHERE The Dark Knight premiere in New York City
WHY WE LOVE IT "It’s a floral yet there’s something dark and mysterious about it. It’s not the kind of glamour that jumps out and screams at you."

86 of 100 Bauer-Griffin

Natalie Portman in Christian Lacroix

WHERE The Other Boleyn Girl premiere in London
WHY WE LOVE IT "It’s a wonderfully sensuous color on her and the embroidery only enhances the 19th century appeal. I love the off-the-shoulder romance about it."

87 of 100 Kevork Djansezian/AP

Cate Blanchett in Dries Van Noten

WHERE 80th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "It was an unbelievable deep, rich, royal purple with extraordinary beading on the bottom and a neckline made out of sterling silver."

88 of 100 Chris Pizzello/AP

Rihanna in Zac Posen

WHERE 50th Annual Grammy Awards in Los Angeles
WHY WE LOVE IT "This is what you call a real party dress. It moves, it flares, it spins-it’s just what you’d want to wear dancing all night."

89 of 100 Steve Granitz/WireImage

Tilda Swinton in Lanvin

WHERE 80th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "It's deliberately asymmetrical. It’s deliberately unbalanced. The black velvet draped around her ghostlike skin gave the look a haunting, gothic sexiness."

90 of 100 Don Arnold/WireImage

Cate Blanchett in Balenciaga

WHEREThe Curious Case of Benjamin Button premiere in Sydney, Austrailia
WHY WE LOVE IT "It’s the uniqueness of the fabric that’s so stunning because it’s doing sparkle in a completely modern way. The technology of this dress is extraordinary."

91 of 100 Ian West/Abaca

Keira Knightley in Rodarte

WHERE 65th Annual Golden Globes in Los Angeles
WHY WE LOVE IT "The innocence of this dress coupled with Keira’s hair and makeup made her look incredibly virginal. She looked like a girl going to her first party."

92 of 100 Abaca

Amy Adams in Proenza Schouler

WHERE 80th Annual Academy Awards in Los Angeles
WHY WE LOVE IT "It's so sculpted and you can see the construction of the dress when it fully fans out. The color plays against the milky quality of Amy’s skin."

93 of 100 DPA/Landov

Linda Evangelista in Lanvin

WHERE Cannes Film Festival in Cannes, France
WHY WE LOVE IT "It would’ve been a spectacular gown in the '20s, it’s a spectacular gown now and it will be a spectacular gown in 50 years. It’s a traffic-stopping dress."

Kyra Sedgwick, 60th Primetime Emmy Awards, Jeweled Necklines

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Kyra Sedgwick in L'Wren Scott

WHERE 60th Annual Emmy Awards in Los Angeles
WHY WE LOVE IT "This is a great formfitting dress that doesn’t look like she's trying too hard. The beading from the straps across the chest gave it a sexy element without being too revealing."

95 of 100 Frank Micelotta/Getty

Keira Knightley in Vera Wang

WHERE 81st Annual Academy Awards in Los Angeles
WHY WE LOVE IT "It’s intricately draped and gathered then splashes out with just enough train. In this dress, a woman shows up on the red carpet a new-comer and walks away a star."

Freida Pinto, Christian Lacroix,Golden Globes 2009

96 of 100 Steve Granitz/WireImage

Freida Pinto in Christian Lacroix

WHERE 66th Annual Golden Globes in Los Angeles
WHY WE LOVE IT "It was a completely unexpected and surprisingly mature choice. You need a really cool sense of self to wear a dress like this and pull it off."

97 of 100 Pascal Le Segretain/Getty Images

Julianne Moore in Tom Ford

WHERE 66th Annual Venice Film Festival in Venice
WHY WE LOVE IT "I love the deep ‘V’ on the decolletage and then the full V in the skirt. Also, the color is just perfect."

98 of 100 Kevin Mazur/WireImage

Kate Moss in Marc Jacobs

WHERE Costume Institute Gala in New York City
WHY WE LOVE IT "Marc can be elaborate, romantic, grunge or hard, but when he does minimal I think he excels. You really see the power of his dress-making."

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Emma Watson in Burberry Prorsum

WHERE London Fashion Week
WHY WE LOVE IT "You don’t want to overdress or dress beyond your years on the red carpet. I love that this dress is so kicky and young!"

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Camilla Belle in Alexander McQueen

WHERE Push premiere in Los Angeles
WHY WE LOVE IT "There is an absolute fabulousness about this print. It’s this Rorschach pattern that V’s in two directions coming exactly into her waist. The print, as extravagant as it is, is incredibly flattering."