Jennifer Aniston’s 9 Iconic Looks You Can’t Get Out of Your Head

She’s a legend for a reason.

Jennifer Aniston's best looks from the 1995 to today.

Rachel Green may have held the title of TV’s most stylish for a decade, but Jennifer Aniston’s IRL sartorial legacy spans three, surpassing that of her onscreen alter ego. Since she burst onto the scene in the ’90s, America’s sweetheart quickly became a fashion darling.

Her red carpet style, in particular, showcased her affinity for classics that evoked the decade’s minimalism. Think: column dresses, sophisticated neutrals, and understated saucy details. In fact, the Friends actor could teach a masterclass in timeless dressing — her style is just that good.

She developed a signature awards show look in the naughties, making sleek LBDs with cleavage-baring details her signature (a style she still harkens to). And on the rare occasion she strayed from black, in muted pinks or pops of red, she was still the personification of understated elegance.

Ahead, these and more of Aniston’s best looks from her sartorial hall of fame.

A Daring Exposed Bra

Jennifer Aniston wears a black knit top, pants, and heels at the VH1 Honors event in 1995.

To attend the 1995 VH1 Honors awards ceremony, Aniston wore one of her most risqué looks of all time. She flaunted a lacy balconette bra under a see-through crochet cardigan, topping off her ensemble with high-rise trousers, heeled sandals, and a ’90s-era lariat necklace. Her buzziest accessory, however, was “The Rachel” haircut, which would become the most requested hairstyle of the decade.

A Banada Crop & Maxi Skirt

Jennifer Aniston wears a crop top and maxi skirt to the 1999 SAG Awards.

Bandana-style crop tops were already trendy by the time the 1999 Screen Actors Guild awards rolled around. However, the typically casual item was made red carpet-appropriate when Aniston pulled up in a sleek, satin iteration. Hers was strapless, silken, and in classic noir — all details that effectively elevated the piece. Paired with a low-rise slip skirt, it was a perfectly ’90s look.

This Striking Red Number

Brad Pitt in Hedi Slimane and Jennifer Aniston in Prada at the 2000 Emmy Awards on September 10, 200...

Aniston attended the 52nd Emmy Awards and veered from her neutral color palette. Instead, she wore a ruby red number by Prada. While the pop of color was unusual, the sleek silhouette (a strapless column) was squarely in her minimalist wheelhouse.

With her then-husband Brad Pitt by her side, it was one of her biggest red carpet hits. Even Aniston seemed to think so — a year later, she recreated the look in an episode of Friends, and again on the red carpet in 2013 (more on that later).

Her Plunging LBD

Jennifer Aniston wears a black halter dress at the Vanity Fair Party held at Morton's for the 72nd A...

That same year, the Morning Show star made her Academy Awards debut on March 2, 2000, wearing a show-stopping halter with a deep, deep neckline. The first of many plunging looks to come, this gown set the tone for her awards show style. Peep her diamond-encrusted choker, which added a glamorous touch.

An Elegant Black Suit

Jennifer Aniston arrives for the Golden Globe Awards on January 20, 2002.

While Aniston loves a little black dress for the red carpet, she switched things up at the 2002 Golden Globes in a two-piece suit. She went bare under her suit jacket to emphasize the deep-V neckline and show a sliver of trendy tummy. However, it was the Murder Mystery star’s simple sparkler — a diamond-encrusted necklace — that sent the corporate-inspired ’fit into luxe territory.

A Dainty Pink Dress

Jennifer Aniston (Photo by Jeff Kravitz/FilmMagic)

Aniston kept to her usual décolletage-flaunting silhouette at the 2002 Emmys, but the similarities stop there. She veered sharply from her typical style in a dreamy, muted pink Dior gown with intricate embroidery. In lieu of jewelry, she wore a scarf draped backwards for a choker-style appearance — a styling trick we should all take note of.

Stacked Keyhole Cut-Outs

Jennifer Aniston wears a Giorgio Armani LBD at the SAG Awards 2003.

By 2003, Aniston had made a noticably edit to her signature plunging LBD by adding one saucy design element: cut-outs. She debuted the look at the SAG Awards, where she was nominated for Female Actor in a Comedy Series.

From Giorgio Armani, the sophisticated column was accented with two cut-outs in front and another two on the back — the perfect balance of elegance and spice. She would recreate the style repeatedly throughout her career, even wearing a nearly identical dress a year later, to the 2004 Golden Globes.

A Dramatic Train

Jennifer Aniston arrives at the Oscars at Hollywood & Highland Center on February 24, 2013.

It takes a real style icon to draw inspiration from your own closet and Aniston fits the bill. In 2013, the actor attended the Oscars wearing an iteration of her 2000 Emmys dress. Instead of a column silhouette, however, her Valentino Haute Couture number featured a voluminous skirt for added drama.

Another Plunging Suit

Jennifer Aniston arrives at the 20th Annual Critics' Choice Movie Awards on January 15, 2015 in Los ...

Another style Aniston returned to? Elegant suiting. She gave her ’02 set an update in 2015 for the Critics’ Choice Movie Awards. Her wine red two-piece had the deepest cleavage dip, which was accentuated by a glimmering gold body chain. A vision in Gucci.

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