100 Best Dresses of the Decade

By 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

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Kate Hudson in Versace

SGranitz/WireImage

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
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Anne Hathaway in Armani Prive

Mario Anzuoni/Landov

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 101

Charlize Theron in Vera Wang

Rob Beccaris/WireImage

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."
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Eva Mendes in Dior

Steve Granitz/WireImage

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 101

Penelope Cruz in Atelier Versace

Steve Granitz/WireImage

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."

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Gwen Stefani in Valentino

Paul Smith/Featureflash/Retna

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.”
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Jessica Alba in Dolce & Gabbana

Evan Agostini/Getty Images

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."

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Kate Winslet in Atelier YSL

Steve Granitz/WireImage

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."

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Sarah Jessica Parker in Chanel

Fernando Allende/CelebrityPhoto

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."
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Drew Barrymore in Alberta Ferretti

Dave Allocca/Startraks Photo

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."

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Joy Bryant in Donna Karan

Gregg DeGuire/WireImage

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."

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Reese Witherspoon in Nina Ricci

Frazer Harrison/Getty

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."

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Jennifer Lopez in Versace

Fitzroy Barrett/Globe Photos

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."

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Cate Blanchett in Prada

Dave Hogan/Getty Images

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."

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SJP in Richard Tyler

Jim Smeal/WireImage

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."
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Uma Thurman in Jean Paul Gaultier

Frank Micelotta/Getty Images

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."

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Halle Berry in Valentino

Jeffrey Mayer/Wireimage

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."

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Charlize Theron in Narciso Rodriguez

Steve Granitz/WireImage

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."
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Penelope Cruz in Ralph Lauren

KMazur/WireImage

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."

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Demi Moore in Donna Karan

Evan Agostini/ImageDirect/Getty Images

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 101

Kate Beckinsale in Givenchy

Jon Furniss/WireImage

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."
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Michael Michele in Hermes

SGranitz/WireImage

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 101

Julianna Margulies in Oscar De La Renta

Fitzroy Barrett/Globe Photos

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 101

Nicole Kidman in Jean Paul Gaultier

Dave Hogan/Getty Images

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."
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Jennifer Lopez in Alexander McQueen

Theo Wargo/WireImage

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 101

Jennifer Connelly in Vivienne Westwood

Dave Hogan/Getty Images

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."

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Heather Locklear in Michael Kors

Gilbert Flores/Celebrity Photo

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."
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Oprah Winfrey in Bradley Bayou

Gilbert Flores/Celebrity Photo

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."

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Halle Berry in Collette Dinnigan

SGranitz/WireImage

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 101

Kate Beckinsale in Gucci

SGranitz/WireImage

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."
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Kate Hudson in Valentino

KMazur/WireImage

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 101

Gwen Stefani in Vivienne Westwood

KMazur/WireImage

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 101

Selma Blair in Behnaz Sarafpour

Carmen Valdes/Ron Galella/WireImage

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."
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Renee Zellweger in Carolina Herrera

Jean-Paul Aussenard/WireImage

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 101

Victoria Beckham in Dolce & Gabbana

Gregg DeGuire/WireImage

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 101

Diane Lane in Oscar De La Renta

SGranitz/WireImage

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."
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37 of 101

Kate Hudson in Jean Paul Gaultier

Mirek Towski/Filmmagic

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 101

Scarlett Johansson in Calvin Klein

eter Kramer/Getty Images

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 101

Natalie Portman in Stella McCartney

Rabbani and Solimene Photography/WireImage

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."
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40 of 101

Julia Roberts in Armani

SGranitz/WireImage

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 101

Nicole Kidman in Chanel

Hahn-Khayat-Nebinger/Abaca

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 101

Kelly Rowland in Dolce & Gabbana

Jeffrey Mayer/WireImage

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."
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43 of 101

Jennifer Lopez in Michael Kors

Mark J. Terrill/AP Photo

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 101

Thandie Newton in Miu Miu

Gregg DeGuire/WireImage

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 101

Kristen Davis in Prada

Gilbert Flores/Celebrity Photo

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."
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46 of 101

Sheryl Crow in Narsico Rodriguez

KMazur/WireImage

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 101

Gwen Stefani in Vivienne Westwood

KMazur/WireImage

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 101

Jennifer Garner in Valentino

Steve Granitz/WireImage

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."
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49 of 101

Kate Bosworth in Louis Vuitton

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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 101

Bridget Moynahan in Narciso Rodriguez

Fernando Allende/Celebrity Photo

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 101

Kelly Ripa in Oscar De La Renta

Barry Talesnick/IPOL/GLOBE PHOTOS

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."
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Ellen Pompeo in Prada, 2004

Dave M. Benett/Getty Images

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."

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Hilary Swank in Guy Laroche

SGranitz/WireImage

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 101

Kate Hudson in Roberto Cavalli

Tim Whitby/WireImage

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."
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Gwyneth Paltrow in Stella McCartney

Carlo Allegri/Getty Images

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."

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Salma Hayek in Prada

Carlo Allegri/Getty Images

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."

57 of 101

Eve in Louis Vuitton

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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."
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Kristen Scott Thomas in YSL

Badi-Ftw-Sam/Starface/Retna

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 101

Scarlett Johansson in Roland Mouret

Jason Merritt/FilmMagic

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 101

Sienna Miller in Dior

George Pimentel/WireImage

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."
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Hilary Swank in Calvin Klein

Carlo Allegri/Getty Images

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."

62 of 101

Halle Berry in DvF

Dave Allocca/Startraks

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 101

Amy Adams in Carolina Herrera

Frazer Harrison/Getty Images

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."
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