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    Jennifer Aniston: Her 20 Sexiest Fashion Moments

    Some call her style predictable or boring, but we think Jennifer Aniston has cornered the celebrity market on effortlessly chic style. She rarely makes a misstep on the red carpet, and what's more, she seems to only get better with age like a fine wine. Aniston manages to walk the delicate line between edgy and girl-next-door, and she always looks hot doing it.

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  • Emmy Awards, 2000
    In a rare break from her usual black, Aniston, who was nominated that year for Best Supporting Actress on "Friends," looked stunning in a bright red, strapless Prada gown.
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    Reuters
  • Golden Globe Awards, 2002
    Nominated again for her work on "Friends," Aniston was the epitome of understated elegance at the 2002 Golden Globe awards, opting for a black tuxedo suit with a stunning diamond necklace to add some flair.
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    Reuters
  • The GLAAD Media Awards, 2007
    Wearing her signature color, Aniston embraced an edgier look in this shimmering little black dress from Chanel.
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    Reuters
  • Aniston looked gorgeous in this vibrant Valentino number, another perfect little black dress.
    Aniston looked gorgeous in this vibrant Valentino number, another perfect little black dress.
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    Reuters
  • It's hard to make a suit look this sexy, but Aniston made it look easy in a low-cut Burberry pantsuit.
    It's hard to make a suit look this sexy, but Aniston made it look easy in a low-cut Burberry pantsuit.
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    Reuters
  • Oscars, 2009
    Aniston attended the awards that year with her then-boyfriend, musician John Mayer, and dazzled on the red carpet in a Valentino Haute Couture gown.
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    Reuters
  • Aniston sparkled in a super-short silver Valentino mini-dress, showing off her famous legs and age-defying body.
    Aniston sparkled in a super-short silver Valentino mini-dress, showing off her famous legs and age-defying body.
    read more
    Reuters
  • In contrast to her normal style, Aniston donned a draped Grecian-style gown by Donna Karan, wearing it with confidence.
    In contrast to her normal style, Aniston donned a draped Grecian-style gown by Donna Karan, wearing it with confidence.
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    Reuters
  • Aniston looked red hot in a short Valentino dress complemented with an Alexander McQueen tuxedo jacket.
    Aniston looked red hot in a short Valentino dress complemented with an Alexander McQueen tuxedo jacket.
    read more
    Reuters
  • Elle's Women in Hollywood Tribute, 2011
    Playing up her sexy side, Aniston opted for a sequin KaufmanFranco dress (featuring a plunging neckline) along with a Ferragamo clutch.
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    Reuters
  • Aniston shed her "girl next door" image in a racy leather Celine dress.
    Aniston shed her "girl next door" image in a racy leather Celine dress.
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    Reuters
  • Aniston shocked all when she opted for a pattern on the red carpet, which she did SO stylishly in a Tom Ford bustier dress.
    Aniston shocked all when she opted for a pattern on the red carpet, which she did SO stylishly in a Tom Ford bustier dress.
    read more
    Reuters
  • Aniston looked effortlessly stylish — while rocking an amazing figure — in a basic white tank and a shiny navy skirt.
    Aniston looked effortlessly stylish — while rocking an amazing figure — in a basic white tank and a shiny navy skirt.
    read more
    Reuters
  • Emmy Awards, 2002
    In 2002, a year that was filled with accolades for Aniston, she received the award for Outstanding Lead Actress in a Comedy Series for her role on "Friends." Aniston attended the ceremony in a dazzling vintage Christian Dior gown and tousled waves.
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    Reuters
  • Aniston opted for a more ladylike look at the London premiere of her movie, wearing a strapless red dress with rosettes.
    Aniston opted for a more ladylike look at the London premiere of her movie, wearing a strapless red dress with rosettes.
    read more
    Reuters
  • Cannes Film Festival, 2004
    Attending the "Troy" premiere with then-husband Brad Pitt, Aniston looked stunning in an Atelier Versace white gown.
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    Reuters
  • Emmy Awards, 2004
    A nominee for Best Lead Actress in a Comedy Series for her role on "Friends," Aniston looked amazing in a Chanel Haute Couture gown with Fred Leighton earrings.
    read more
    Reuters
  • Oscars, 2006
    A presenter that year, Aniston opted for understated elegance in a delicate black Rochas gown with Rochas jewelry.
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    Reuters
  • Sporting an uncharacteristic ponytail, Aniston looked playful and elegant in a ruffly and sheer Yves Saint Laurent ensemble.
    Sporting an uncharacteristic ponytail, Aniston looked playful and elegant in a ruffly and sheer Yves Saint Laurent ensemble.
    read more
    Reuters
  • Aniston, who was rumored to be dating co-star Vince Vaughn at the time, set off an "I want that dress!" craze after she appeared on the red carpet in this sexy BCBG Max Azria cocktail dress.
    Aniston, who was rumored to be dating co-star Vince Vaughn at the time, set off an "I want that dress!" craze after she appeared on the red carpet in this sexy BCBG Max Azria cocktail dress.
    read more
    Reuters
  • Published
    21 Images

    Jennifer Aniston: Her 20 Sexiest Fashion Moments

    Some call her style predictable or boring, but we think Jennifer Aniston has cornered the celebrity market on effortlessly chic style. She rarely makes a misstep on the red carpet, and what's more, she seems to only get better with age like a fine wine. Aniston manages to walk the delicate line between edgy and girl-next-door, and she always looks hot doing it.

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  • Jennifer Aniston: Her 20 Sexiest Fashion Moments
  • 1
  • Emmy Awards, 2000
  • Golden Globe Awards, 2002
  • The GLAAD Media Awards, 2007
  • Aniston looked gorgeous in this vibrant Valentino number, another perfect little black dress.
  • It's hard to make a suit look this sexy, but Aniston made it look easy in a low-cut Burberry pantsuit.
  • Oscars, 2009
  • Aniston sparkled in a super-short silver Valentino mini-dress, showing off her famous legs and age-defying body.
  • In contrast to her normal style, Aniston donned a draped Grecian-style gown by Donna Karan, wearing it with confidence.
  • Aniston looked red hot in a short Valentino dress complemented with an Alexander McQueen tuxedo jacket.
  • Elle's Women in Hollywood Tribute, 2011
  • Aniston shed her "girl next door" image in a racy leather Celine dress.
  • Aniston shocked all when she opted for a pattern on the red carpet, which she did SO stylishly in a Tom Ford bustier dress.
  • Aniston looked effortlessly stylish — while rocking an amazing figure — in a basic white tank and a shiny navy skirt.
  • Emmy Awards, 2002
  • Aniston opted for a more ladylike look at the London premiere of her movie, wearing a strapless red dress with rosettes.
  • Cannes Film Festival, 2004
  • Emmy Awards, 2004
  • Oscars, 2006
  • Sporting an uncharacteristic ponytail, Aniston looked playful and elegant in a ruffly and sheer Yves Saint Laurent ensemble.
  • Aniston, who was rumored to be dating co-star Vince Vaughn at the time, set off an "I want that dress!" craze after she appeared on the red carpet in this sexy BCBG Max Azria cocktail dress.
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