(Celebrity)

This Outfit From 1999 Is Jennifer Aniston's Best Look Ever

It still works today.

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Jennifer Aniston most iconic outfits

Sure, Gen Z is obsessed with replicating the looks of TV’s arguably best-dressed but least-experienced coffee shop waitress turned fashion executive Rachel Green: The baby tees, knee socks, and slip dresses are exactly the kind of nostalgic, 90s style that’s seemingly everywhere again. That said, an effortlessly cool wardrobe has also been a constant for the actor behind the beloved Friends character as well — both on screen and off. Throughout her decade-spanning career, Jennifer Aniston’s most iconic outfits prove she’s a reliable source of inspiration, having sported countless casually chic yet sensual looks that are as timeless as she is.

The 52-year-old actor — who will soon reprise her star-making role in the recently announced reunion — 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.

1995

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Jen showed a sexier side at the 1995 VH1 Honors when she turned up in a crocheted top and bra — and of course her signature “The Rachel” ‘do.

1996

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The actor’s love for minimalist looks started early on, as seen here when she wore a nude tank dress to her very first Golden Globes.

1997

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Aniston’s quintessentially 90s black mini dress from her 1997 Cosmopolitan cover party is actually something she’d still probably wear today.

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

Ron Galella/Ron Galella Collection/Getty Images

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.

1999

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At the 1999 Emmys, the actor took another risk when she donned a brown Randolph Duke dress with a sheer, sequined bodice.

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.

2002

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Jen paired beachy waves with her nude Dior dress at the 2002 Emmys — and later accessorized her look with a Lead Actress in a Comedy Series award.

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.

2005

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Another shimmering Chanel dress was Aniston’s choice for the NYC premiere of Derailed.

2006

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For the UK premiere of The Breakup, the star picked a breezy, smokey grey dress with cutouts.

2006

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While doing press for The Breakup in 2006, Aniston wore a gunmetal sequin dress and strappy heels (a forever favorite shoe choice for the actress).

2009

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Jen chose another metallic mini (this time by Prada) for Women In Film’s Crystal and Lucy Awards in 2009.

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 this flesh-colored dress trend.

2016

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The LBD fan showed a lighter, more ethereal side in this floaty Saint Laurent look at the 2016 Critic’s Choice Awards.

2016

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While attending the premiere for Office Christmas Party, Aniston wore a Roberto Cavalli dress that embraced her bohemian spirit.

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 this Chanel 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.