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Jennifer Aniston: Her 20 Sexiest Fashion Moments

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.

(Reuters)
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.

(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.

(Reuters)
"The Good Girl" Premiere, 2002

Aniston looked effortlessly stylish — while rocking an amazing figure — in a basic white tank and a shiny navy skirt.

(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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"Along Came Polly" Premiere, 2004

Aniston opted for a more ladylike look at the London premiere of her movie, wearing a strapless red dress with rosettes.

(Reuters)
Cannes Film Festival, 2004

Attending the "Troy" premiere with then-husband Brad Pitt, Aniston looked stunning in an Atelier Versace white gown.
 

(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.

(Reuters)
Oscars, 2006

A presenter that year, Aniston opted for understated elegance in a delicate black Rochas gown with Rochas jewelry.

(Reuters)
"Friends With Money" Premiere, 2006

Sporting an uncharacteristic ponytail, Aniston looked playful and elegant in a ruffly and sheer Yves Saint Laurent ensemble.

(Reuters)
"The Break Up" Premiere, 2006

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.

(Reuters)
The GLAAD Media Awards, 2007

Wearing her signature color, Aniston embraced an edgier look in this shimmering little black dress from Chanel.

(Reuters)
"Marley & Me" Premiere, 2008

Aniston looked gorgeous in this vibrant Valentino number, another perfect little black dress.

(Reuters)
"He's Just Not That Into You" Premiere, 2009

It's hard to make a suit look this sexy, but Aniston made it look easy in a low-cut Burberry pantsuit.

(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.

(Reuters)
"Love Happens" Premiere, 2009

Aniston sparkled in a super-short silver Valentino mini-dress, showing off her famous legs and age-defying body.

(Reuters)
"The Bounty Hunter" L.A. Premiere, 2010

In contrast to her normal style, Aniston donned a draped Grecian-style gown by Donna Karan, wearing it with confidence.

(Reuters)
"The Bounty Hunter" London Premiere, 2010

Aniston looked red hot in a short Valentino dress complemented with an Alexander McQueen tuxedo jacket.

(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.

(Reuters)
"Horrible Bosses" Media Event, 2011

Aniston shed her "girl next door" image in a racy leather Celine dress.

(Reuters)
"Wanderlust" Premiere, 2012

Aniston shocked all when she opted for a pattern on the red carpet, which she did SO stylishly in a Tom Ford bustier dress.
 

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