(Celebrity)

Jennifer Aniston's Outfit From 1999 Is An Unforgettable One

A Rachel Green-approved look.

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Jennifer Aniston at the 20th annual Critics' Choice Movie Awards.

In the ‘90s, Jennifer Aniston became a notable style icon thanks to her playing everyone’s favorite on-screen fashionista Rachel Green in Friends. The actor had a similar wardrobe as Green IRL, as they both adored the ‘90s fashion trends of slip dresses, knee-high socks, and miniskirts. Presently, Aniston still retains the badge of honor as a style queen, but her wardrobe has evolved to become more minimalistic and classic. (Think pieces that are less trend-driven and more timeless like a sleek trench coat or an everyday Celine handbag.) Over the years, Aniston’s most iconic outfits, from her countless casually chic outfits to glammed-up looks, served as reliable sources of dressing inspo for many fans.

The 52-year-old actor has no doubt opted for more daring, statement-making ensembles when the occasion calls for one — like her plunging V-neck dress at the 2017 Vanity Fair Oscar party. From her best looks to date, it’s clear that she knows what she likes — neutral tones over flashy colors. That goes for her accessories on or off the red carpet as well. When she’s not working, she prefers her daily black crossbody bags and gravitates towards minimalist clutches or pouches for celebrity events.

That said, even The Morning Show actor is not immune to an of-the-moment trend or two as they come along such as wide-leg trousers or the classic ‘90s fall combo of a leather jacket and jeans. Yet, in true Aniston fashion, she manages to make these trendy themes feel timeless. In particular, throughout her years on the red carpet, whether she’s making an appearance at a low-key media event or attending a major awards ceremony, Aniston’s given the world a virtually endless collection of stylish ensembles anyone can appreciate.

Ahead, you’ll see how the actor has adapted her style over the years through her most iconic looks yet.

26th Screen Actors Guild Awards

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Aniston steers towards a classic style, but that doesn't mean she plays it safe. Her 2020 SAG Awards look proved it. The actor wore a vintage, figure-hugging white silk V-neck dress from Christian Dior by John Galliano. The silky dress had a tie detail on the hip that draped to the floor for a stylish flair.

77th Golden Globe Awards

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At the 2020 Golden Globe Awards, Aniston went for a dramatic black strapless ball gown. The stylish Dior Haute Couture number featured soft ruffle details along the bodice, which created a sophisticated and romantic appearance. She also cinched in her waist (to account for the voluminous bodice) with a nearly invisible skinny black belt. A diamond ring and glistening necklace completed the look.

2018 Chanel x National Resources Defense Council Party

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In 2018, Aniston attended the Chanel and NRDC benefit while wearing a full head-to-toe black ensemble from the French fashion house. A tank top was tucked into a pair of polished wide-leg trousers, which featured two rows of matching buttons. For a casual, but fashion girl-approved touch, the actor draped a cropped blazer over her shoulders instead of slipping it on all the way.

2017 Vanity Fair Oscars Party

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Thigh-high splits and a plunging V-neck are two common details you can find in Aniston’s dresses for red carpet events. These daring designs were of course present in Aniston’s party look at the 2017 Vanity Fair Oscar after-party. She wore a bold black sequined dress from Atelier Versace with matching colored heels.

2016 Premiere For Office Christmas Party

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While attending the premiere for Office Christmas Party in 2016, the actor wore a Roberto Cavalli dress that embraced her bohemian side. The floor-length dress featured a variety of colorful whimsical floral prints and had a V-neck design. She kept her accessories pared-back, opting for warm gold tones via a clutch and bangles.

21st Critics' Choice Awards

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At the 2016 Critics’ Choice Awards, Aniston matched the blue carpet in her Yves Saint Laurent dress. The breezy gown featured a middle split, which revealed her strappy heels underneath — also in a blue hue. The ensemble felt breezy and casual as opposed to an overly opulent gown. Her go-to accessories for this soft look were a pair of dainty drop earrings and layered diamond necklaces.

83rd Academy Awards

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Aniston’s 2015 Oscar outfit was a bit of a surprise, as the actor doesn’t usually go for a nude-colored gown at award shows. Here, she sported a figure-hugging, semi-sheer number by Versace. The one-shoulder, shiny number draped to the floor and featured a sweetheart neckline. When you look back at this dress, it still feels appropriate even for today’s red carpet events.

85th Academy Awards

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For those who tuned into the 2013 Oscars, you witnessed an undoubtedly timeless look from Aniston. The actor wore a custom red strapless gown from Dior for the fancy occasion. All her accessories were styled on her left hand — she wore two diamond bracelets, a ring, and carried a rectangular gold clutch.

67th Golden Globe Awards

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For the 2010 Golden Globe Awards, the actor took her style to the edgier side with a floor-length, one-shoulder black gown. It featured a thigh-high slit, which showed off her strappy sandals. The actor completed her daring look with multiple bangles, an accessory she frequently rocks on the red carpet.

2009 Women In Film’s Crystal & Lucy Awards

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Aniston chose a simple, but fashion-forward metallic Prada mini dress for the Women In Film’s Crystal and Lucy Awards in 2009. The dress was strapless and had a low, heart-shaped neckline. For her shoes, she went with nude heels and kept the accessories to a minimum with only a ring on her finger.

2006 Press Tour For The Breakup

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While doing press for The Breakup in 2006, Aniston wore a spaghetti strap gunmetal, knee-length dress. It was decked out in sequins and she accessorized with a pair of silver mule heels, which are currently trending with the fashion crowd. In usual Aniston fashion, she wore a no-makeup, makeup look for that effortless Cali-girl vibe.

2006 Premiere Of The Breakup

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Remember halter-neck dresses from the early aughts? Aniston proved she was able to pull off that trend in this LBD when she attended the premiere of The Breakup in 2006. The dress also featured a flirty side cutout and a pleated bodice for those subtle but cool details. Here, Aniston again opted for the “less is more” approach when it came to her jewelry.

2005 Premiere Of Derailed

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The actor loves a good shimmery dress as evidenced by this knee-length style. The design resembled fine grains of sand glittering underneath the sun. She wore the cocktail dress to the New York City premiere of her 2005 movie Derailed. A pair of chandelier earrings and matching gold sandals, plus clutch, completed the outfit.

56th Primetime Emmy Awards

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Aniston sure loves her white and gold ensembles for the red carpet. At the 2004 Emmys, she wore a gold metallic-accented, floor-length dress. The strapless number was from Chanel. Again, the actor chose to keep her jewelry on the subtle side, opting for a thin bracelet, some rings, and drop earrings.

2004 Cannes Film Festival

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At the 2004 Cannes Film Festival, Aniston embraced the trendy halter-neck style in the form of a shimmery, figure-hugging Versace dress. The actor’s red carpet number had criss-cross gold sequined details that continued all the way down the dress. In addition, the hemline flared out slightly at the bottom for a little bit of dramatic flair.

9th Screen Actors Guild Awards

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Aniston wore for a flirty red carpet look to the 2003 Screen Actors Guild Awards. The striking navy dress featured two risky cutouts in the front — a detail that would still be on trend today. When it came to her accessories, Aniston wore a dazzling diamond bracelet and held a black clutch.

54th Primetime Emmy Awards

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At the 2002 Emmys, Aniston wore her hair in loose beach waves with her glamorous pale pink Dior dress. The designer gown featured a generous scoop-neck design while sequins detailed the bodice and hip area. That night, Aniston won an Emmy for Lead Actress in a Comedy Series for her work in Friends.

52nd Primetime Emmy Awards

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For the 2000 Emmys, the Friends actor wore a minimalist, cherry-colored spaghetti strap column gown. She paired the bright look with a diamond bracelet and a dainty diamond necklace. On her shoulder was a small shoulder bag, which has since returned with vigor in the fashion world via baguette styles and the like.

51st Primetime Emmy Awards

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At the 1999 Emmys, the actor made a brave fashion move when she donned a Randolph Duke dress, which had a sheer gold sequined bodice and a plum brown fitted skirt. Her ensemble gave off a bohemian feel when styled with loose, braided waves. As for accessories, she wore gold bangles and carried a clutch.

5th Screen Actor Guild Awards

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At the 1999 SAG Awards, Aniston wore a navy silk bandana-style top with a pleated maxi skirt of the same hue. Years later, this “scarf as a top” look became a beloved summer 2021 trend that all it-Girls channeled. Unlike Aniston, you can style your top with more casual bottoms like jeans or even denim shorts.

1997 Premiere Of Picture Perfect

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Florals never go out of style, just ask Aniston. The actor attended the 1997 premiere of Picture Perfect while wearing a romantic and classic floral dress. She accessorized with a small shoulder bag. This throwback look would still hold up today, which is a testament to the actor’s timeless style.

1997 Cosmopolitan Cover Party

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The actor loved a good ol’ LBD back in the ‘90s and she still does so today. Here, Aniston posed next to her 1997 Cosmopolitan cover at a party hosted for the actor. The black spaghetti strap mini dress can be seen on celebrities today like Hailey Bieber and Kendall Jenner.

53rd Golden Globe Awards

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The actor’s love for minimalist looks started early on. For her very first Golden Globes in 1996, Aniston wore a beige tank dress and brown pointy heels. She also went for a no-makeup, makeup look. Meanwhile, her Friends costars Lisa Kudrow and Courteney Cox went for more traditional red-carpet glam ensembles. Everyone looked amazing, though.

1995 Logo Trailblazers Honors Event

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While the one-button style hack is often associated with Gigi Hadid, Bella Hadid, and Rihanna, the trend could be linked back to Aniston in the ‘90s. At the 1995 VH1 Honors event, Aniston wore a bralette under a crochet cardigan, which was held together by a single button. The only accessory she wore with the risky outfit was a long necklace.

1990 National Broadcasting Company’s Allstars Party

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Aniston’s fashion in the ‘90s was relatable, as she wore baggy mom jeans and casual button-down silk shirts. At the NBC Allstars Party in 1990, her casual denim outfit gave off laid-back, West Coast vibes. Though Aniston would likely dress up just a tad bit more present day, this look is still so iconic.