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

It still works today.

Originally Published: 
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.


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


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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.


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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.


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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.


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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.


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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.


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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.


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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.


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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.


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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.


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


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


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


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


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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).


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


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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.


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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.


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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.


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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.


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


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


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In 2018, Aniston attended this Chanel party wearing a full ensemble from the French fashion house.


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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.


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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.