Fame10 Fashion Evolution: Jennifer Aniston

Published on October 31, 2014. Updated April 4, 2017

Jennifer Aniston has one of the best bodies in the business and one of the most envied heads of hair in Hollywood. These two things alone, however, aren’t enough to make her a stylish star. After carefully examining her fashion choices, we’ve come to the conclusion that Jen likes to play it safe on the red carpet. She doesn’t typically wear any color and instead opts for simple dresses with minimal accessories. She never looks bad per say, but she never takes any real chances. Come with us as we take a look at Jennifer Aniston’s fashion evolution!

9th Annual GLAAD Awards – 1998

Jennifer Aniston dressed very differently back in 1998. She wore this figure-hugging cream-colored dress to the 9th Annual GLAAD Awards with a leopard print purse and her glasses. While we like that the dress shows off her amazing figure, we don’t think there is anything particularly attractive about it. The most surprising thing about the ensemble is the fact that she chose to wear her glasses with it.

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Screen Actors Guild Awards – 1999

The “Friends” star looked gorgeous at the Screen Actors Guild Awards in 1999. She kept everything pretty simple with this black top and black skirt, which showed off her ridiculously toned stomach. This outfit is perfect for Jennifer. Her hair and her body are her greatest assets and this ensemble really lets them both shine.

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Emmy Awards – 2002

From certain angles, this pale pink Christian Dior gown looks really good; however, from other angles, it isn’t flattering. The scarf doesn’t really compliment the dress and the front of the dress hangs a bit too low. Her best accessory at 2002 Emmy Awards was definitely her gorgeous husband, Brat Pitt.

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9th Annual Screen Actors Guild Awards – 2003

This blue gown that Jennifer Aniston wore to the 9th Annual Screen Actors Guild Awards is interesting. The cutouts definitely give it more character. When you have a body as amazing as hers, you definitely should show it off. We’re not sure what Courteney Cox is wearing, but it looks pretty tragic.

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56th Annual Primetime Emmy Awards – 2004

The budding movie star looked amazing at the 56th Annual Primetime Emmy Awards in this white Chanel column gown with gold beaded details. This is one of our favorite red carpet looks on Jennifer Aniston. She looks like the quintessential California girl with her wavy blond locks.

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Premiere of Rumor Has It – 2005

Jennifer Aniston wore this sheer strapless black column gown to the premiere of “Rumor Has It.” We really like this dress – it is absolutely beautiful; however, we are noticing a certain trend with Aniston – she wears a lot of neutral-colored dresses on the red carpet. This gown would have been more interesting if she had chosen a different, more vibrant, color. Black is too safe.

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78th Annual Academy Awards – 2006

The “Break Up” star sported a black Rochas gown with a vintage Bulgari diamond necklace and a Lana Marks alligator clutch at the 78th Annual Academy Awards. This dress is exquisite; however, we wish it was in a different color. She wears way too much black and doesn’t take enough risks on the red carpet.

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33rd Annual People’s Choice Awards – 2007

Jennifer switched things up for the 33rd Annual People’s Choice Awards. She donned this sparkling cream-colored Versace dress, which is a definite improvement over past looks since it’s not black. Maybe at the next event she will wear something with more color!

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Premiere of Love Happens – 2009

This is one of the most adventurous dresses the “Good Girl” star has ever worn on the red carpet and we love it! She shined at the premiere of “Love Happens” thanks to this short, sparkly Valentino dress paired with Christian Louboutin strappy-jeweled sandals. If only she took risks like this more often!

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Premiere of The Switch – 2010

Jennifer Aniston wore her two favorite colors to the premiere of “The Switch” – black and beige. While we do think this Lanvin dress is nice – after all, it does show off her amazing legs – we also find it really boring. She really needs a stylist. Maybe Rachel Zoe will take her on as a client.

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Handprint & Footprint Ceremony – 2011

The former television star tried a different look at her Handprint & Footprint Ceremony. She wore this floral-printed Prada dress with nude Gucci heels. We love how Jennifer Aniston looks with a bit of color; however, this dress is ill-fitted. She really should have had it tailored so it didn’t bulge out in weird ways.

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Premiere of Wanderlust – 2012

Jen hit the red carpet in this chevron-print Tom Ford dress, which featured leather trim and peplum. This dress is a definite improvement over many of the other boring black dresses that she has rocked at various other red carpet events; however, we’re still hoping to see her in some color at some point.

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85th Academy Awards – 2013

Jennifer Aniston stepped outside her comfort zone for the 85th Academy Awards in this red Valentino gown with a strapless bodice and full skirt. We wanted more and color and now we have it! However, now a part of us is wondering if she would have looked even more amazing with an updo.

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Premiere of Life of Crime

Jennifer Aniston probably should have gone with a different dress for the premiere of “Life of Crime.” She wore this Saint Laurent mini with a low-cut neckline with a double-breasted blazer, which made her look pregnant. Considering she has one of the fittest bodies in Hollywood, we are amazed that a simple little dress could do that to her.

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