Jennifer Aniston's Outfit From 1999 Is An Unforgettable One

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.