200 Celebrity Looks We Love

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200 Celebrity Looks We Love

David Fisher / Rex USA, Dimitrios Kambouris/WireImage, Baverel-Garcia / Starface / Retna Ltd.

To celebrate our 200th issue, InStyle fashion director Hal Rubenstein handpicked 20 of Hollywood’s best-dressed women, each in 10 quintessential looks. Yes, that’s right-200 iconic fashion moments, from Beyonce’s straight-off-the-runway turn in Balmain to Natalie Portman's stunning Givenchy. Check out our 200 favorites, starting with our current cover girl Gwyneth Paltrow.

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Gwyneth Paltrow in Stella McCartney, 2008

Dimitrios Kambouris/WireImage

“Paltrow gives the illusion of giving something away, while still having a kind of ladylike reserve," says InStyle fashion director Hal Rubenstein. "This sexy mini, by pal Stella McCartney, plays up her best assets and shows off her killer body.”

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Gwyneth Paltrow in Donna Karan, 2009

Pascal Le Segretain/Getty Images

WHY WE LOVE IT

"This gown was custom-made for Gwyneth," says Donna Karan of her design. "It's so ethereal and perfect with her coloring."

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Gwyneth Paltrow in Lanvin, 2008

Romaniello/Venturelli/Olycom/iPhoto

WHY WE LOVE IT

Leave it to Mrs. Chris Martin to give Lanvin's goddess dress a rocker edge with Balmain gladiator heels.

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Gwyneth Paltrow in Stella McCartney, 2005

Gilbert Flores/CelebrityPhoto

WHY WE LOVE IT

This Stella McCartney seems fit for a 21st-century princess, worn with deco-inspired diamonds and a structured clutch.

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Gwyneth Paltrow in Marni, 2009

Venturelli/WireImage

WHY WE LOVE IT

In Marni at an event in Milan, she changes up her natural beauty routine with red lips, dark nails, and an angled bob.

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Gwyneth Paltrow in Valentino, 2002

Camilla Morandi/Rex USA

WHY WE LOVE IT

Sleek equals stunning: At the Venice Film Festival, the star wears this Valentino number with straight hair and a leather cuff.

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Gwyneth Paltrow in Alice + Olivia, 2009

Christopher Peterson/BuzzFoto/FilmMagic

WHY WE LOVE IT

Unafraid to try out new trends, Paltrow combines two cool ones in an Alice + Olivia metallic trench and Christian Louboutin cage heels.

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Gwyneth Paltrow in Calvin Klein, 1996

Ke.Mazur/WireImage

WHY WE LOVE IT

In this Calvin Klein gown at the Oscars, she shows a "love for sensual simplicity" that "makes this woman a classic," says Klein.

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Gwyneth Paltrow in Balenciaga, 2005

Richard Young/Rex USA

WHY WE LOVE IT

Her choice of Balenciaga's long military coat, ruffled top, and cropped pants is just the right mix of masculine and feminine.

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Gwyneth Paltrow in Elie Saab, 2010

Sipa

WHY WE LOVE IT

With minimal jewelry and her hair pulled back, the mom of two lets this crystal-embroidered Elie Saab take center stage.

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Julia Roberts in Valentino, 2001

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“Instead of using a stylist to pick a gown for her Oscar-winning night, Roberts turned to her niece, Emma. This Valentino number gave a huge boost to vintage," says InStyle fashion director Hal Rubenstein.

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Julia Roberts in Giorgio Armani, 2004

Ron Cruz/Thomas Lau

WHY WE LOVE IT

The mom-to-be glowed at the Oscars in a simple yet stunning Giorgio Armani satin gown and Cathy Waterman earrings.

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Julia Roberts in Lanvin, 2009

Villard/Sipa

WHY WE LOVE IT

Cartier jewels gave a luxe touch to her Lanvin gown, but she kept it casually chic with her loose, wavy hairstyle.

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Julia Roberts in Vivienne Tam, 1999

Krista Kennell/Eyedea

WHY WE LOVE IT

At the London première of Notting Hill, the Georgia native set off a vibrant Vivienne Tam sheath with black accessories.

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Julia Roberts in Calvin Klein, 1999

Paul Smith/Retna

WHY WE LOVE IT

Roberts showed that understated doesn't have to mean boring in this sleek Calvin Klein dress. A pink shawl adds punch.

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Julia Roberts in Isaac Mizrahi, 1998

Steve Granitz Archive/WireImage

WHY WE LOVE IT

The actress wore Isaac Mizrahi to accept her sixth People's Choice Award, finishing the look with a ladylike updo.

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Julia Roberts in Georgio Armani Privé, 2008

Dimitrios Kambouris/WireImage

WHY WE LOVE IT

For the Costume Institute Gala, the co-host opted for full-on glamour in a Giorgio Armani Privé gown. Love the brooch!

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Julia Roberts in Giorgio Armani, 2002

Steve Finn/Globe Photos

WHY WE LOVE IT

Her black Giorgio Armani Oscar gown was anything but basic thanks to an up-to-there slit and two well-placed cutouts.

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Diane Kruger in Vivienne Westwood, 2012

Venturelli/WireImage

WHY WE LOVE IT:

Kruger was dripping in (rose) gold as she walked the red carpet at the Cannes premiere of Amour in a Vivienne Westwood draped gown, matching clutch and diamond drop earrings.

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Julia Roberts in Todd Oldham, 1998

Globe Photos

WHY WE LOVE IT

Though she once said "I'll never be a risk taker in fashion," Roberts sparkled in this look-at-me Todd Oldham creation.

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Julia Roberts in Yves Saint Laurent and Esther Chen, 2002

Gilbert Flores/CelebrityPhoto

WHY WE LOVE IT

The secret newlywed hid her ring at a film première with the help of a bell-sleeve YSL blouse and Esther Chen pants.

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Kate Moss in Dior, 2005

Erik C Pendzich/Rex USA

“On the one hand this Dior couture dress is lingerie-inspired and sexy, yet the shape is quite simple. Finishing off the look with tousled bed-head proves that Moss’s instincts are always right," InStyle fashion director Hal Rubenstein says.

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Kate Moss in Kate Moss for Topshop, 2007

Bauer-Griffin

WHY WE LOVE IT

The budding designer works the crowd in a shift with glittering fringe from her Kate Moss Topshop Collection.

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Kate Moss, 1998

Sean Roberts/Everett Collection

WHY WE LOVE IT

Smitten by Julie Christie's dress in Shampoo, Moss dons a striking replica for the CFDA Awards in New York City.

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Kate Moss in Chanel, 2008

Wenn

WHY WE LOVE IT

"Never a fashion victim and the ultimate modern girl," says Karl Lagerfeld of the model, here in his Chanel Haute Couture gown.

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Kate Moss in Siwy and Alexander McQueen, 2008

Dimitrios Kambouris/WireImage

WHY WE LOVE IT

Siwy jeans and a feathered Alexander McQueen vest with a Renee Lewis pendant are casual cool personified.

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Kate Moss in Fendi, 2009

ABACAUSA

WHY WE LOVE IT

At the Fendi O' party for singer Beth Ditto, the trendsetter is a silver stroke of genius in a Fendi dress, fur and shoes.

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Kate Moss in Chanel and Marc Jacobs, 2007

Bauer-Griffin

WHY WE LOVE IT

In a Chanel blouse, Marc Jacobs trousers and her own Topshop belt, she embodies a key commandment: Thou shalt mix high and low.

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Kate Moss in Cerruti, 1997

Sipa

WHY WE LOVE IT

In stark contrast to the Cannes Film Festival's red-carpet glitz, Moss turns heads in a minimalist gray Cerruti sheath.

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Kate Moss in Kate Moss for Topshop, 2009

Turgeon/Rocke/Splash News

WHY WE LOVE IT

Moss dazzles in a beaded peach Kate Moss Topshop Collection dress to fête Topshop's Manhattan arrival.

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Kate Moss in Burberry Prorsum, 2006

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WHY WE LOVE IT

"We wanted something understated but elegant," says Christopher Bailey of the Burberry Prorsum tux he created for the Costume Institute ball.

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Jennifer Aniston in Burberry Prorsum, 2009

Frederick M. Brown/Getty Images

“I love the idea of androgyny," says InStyle fashion director Hal Rubenstein. "And if you’re going to do menswear, you have to sex it up. Aniston really played against type in this Burberry Prorsum pantsuit.”

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Jennifer Aniston in Christian Dior, 2002

Chris Delmas

WHY WE LOVE IT

After winning her Emmy in vintage Christian Dior, the actress donated her gown to a charity auction, fetching $50,000 for Unicef.

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Jennifer Aniston in Chanel, 2007

Janet Gough/CelebrityPhoto

WHY WE LOVE IT

The star accepted the Vanguard Award in this seductive Chanel Haute Couture mini at a GLAAD event.

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Jennifer Aniston in Calvin Klein, 2006

Joerg Carstensen/Wenn

WHY WE LOVE IT

"She makes this dress look effortless and sexy," says Francisco Costa, creative director for women's Calvin Klein Collection.

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200 Celebrity Looks We Love

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200 Celebrity Looks We Love

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Gwyneth Paltrow in Stella McCartney, 2008

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Gwyneth Paltrow in Donna Karan, 2009

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Gwyneth Paltrow in Lanvin, 2008

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Gwyneth Paltrow in Stella McCartney, 2005

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Gwyneth Paltrow in Marni, 2009

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Gwyneth Paltrow in Valentino, 2002

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Gwyneth Paltrow in Alice + Olivia, 2009

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Gwyneth Paltrow in Calvin Klein, 1996

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Gwyneth Paltrow in Balenciaga, 2005

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Gwyneth Paltrow in Elie Saab, 2010

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Julia Roberts in Valentino, 2001

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Julia Roberts in Giorgio Armani, 2004

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Julia Roberts in Lanvin, 2009

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Julia Roberts in Vivienne Tam, 1999

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Julia Roberts in Calvin Klein, 1999

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Julia Roberts in Isaac Mizrahi, 1998

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Julia Roberts in Georgio Armani Privé, 2008

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Julia Roberts in Giorgio Armani, 2002

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Diane Kruger in Vivienne Westwood, 2012

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Julia Roberts in Todd Oldham, 1998

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Julia Roberts in Yves Saint Laurent and Esther Chen, 2002

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Kate Moss in Dior, 2005

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Kate Moss in Kate Moss for Topshop, 2007

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Kate Moss, 1998

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Kate Moss in Chanel, 2008