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A Look At Jennifer Aniston's Most Iconic Outfits Show That Decades Of Timeless Style Can Exist

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When it comes to effortlessly chic and timeless style, no one does it better than Jennifer Aniston. Sure, she may be known for some of the cult-favorite outfits (and hairstyles) worn by her widely beloved character Rachel Green on Friends, but that doesn’t mean her love for fashion stops there. Throughout her decade-spanning career, the actor has shown her penchant for sleek, sexy, and classic silhouettes — and Jennifer Aniston’s most iconic outfits are proof.

The 51-year-old actor has no doubt opted for a more daring, statement-making ensemble when the occasion calls for one. But judging by her best looks to date, it’s clear that she knows what she likes — and because of that, her style is always on point. That said, even The Morning Show actor is not immune to an of-the-moment trend or two as they come along — like the floral-print dresses and shiny tops of the ‘90s. But in true Aniston fashion, she manages to make these once-trendy themes feel ageless.

Throughout her years on the red carpet — whether she was making an appearance at a low-key media event or attending a major awards ceremony — Aniston has given the world a virtually endless collection of stylish ensembles anyone can appreciate. Scroll down to see how the actor has adapted her timeless style over the years through her most iconic looks yet.

1990

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At the NBC Allstars Party in 1990, Aniston keeps her look casual with a button0down shirt and jeans.

1997

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The actor wore a neutral-hued floral-print dress to the New York premiere of Picture Perfect, honing in on popular trends that would transcend time.

1999

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Aniston opted to wear a more daring look for 1999 SAG Awards, pairing a silk bandana-style bandeau — a trend that It girls are wearing everywhere in 2020 — with a pleated maxi skirt.

2000

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For the 2000 Emmys, the Friends actor wore a minimalist-approved red column gown. She kept her look streamlined with diamond jewelry and a baguette handbag.

2003

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Aniston opted for a more alluring look at the Screen Actors Guild 2003, wearing a dress that featured a plunging cutout detail.

2004

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At the 2004 Cannes Film Festival, Aniston embraced the halterneck trend in the form of a glittering Versace dress.

2004

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The actor went with another white and gold dress — this time from Chanel — for the Emmy Awards in 2004.

2010

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To attend the 2010 Golden Globes, Aniston took her style to the edgier side with a floor-length gown featuring a thigh-high slit. The actor completed her look with gold jewelry and strappy sandals.

2013

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The Academy Awards red carpet saw an undoubtedly timeless look from Aniston in 2013. The actor wore a custom dress from Dior for the occasion.

2015

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For the 2015 Oscars, Aniston sported a form-fitting gown by Versace, putting her own spin on the naked dress trend.

2017

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Two years later, Aniston attended the Vanity Fair Oscar party wearing a bold, sequined dress from Atelier Versace.

2018

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In 2018, Aniston attended the Chanel x National Resources Defense Council Party wearing a full ensemble from the French fashion house.

2020

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At the 2020 Golden Globes Awards, Aniston went for an outfit that channeled the sense of drama. The actor wore a gown by Dior Haute Couture gown along with white diamond jewelry.

2020

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Aniston is one for classic style, but that doesn't mean she plays it safe — and her 2020 SAG Awards look proves it. The actor wore a white silk dress from Christian Dior by John Galliano.