Jennifer Aniston’s Style Evolution

Like a true child of the 90’s, Jennifer Aniston played into the big hair and oversized proportions of the time, sporting a boxy blouse tucked into jeans with a chunky looped belt to pull it all together. For the times, this was a clean, classic look that now, in 2019, is having a major moment. Way to start off strong, Jen!

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Looking flawless for any decade in a satin midi dress, strappy heels and hair styled in beachy waves, Jennifer Aniston is giving us all the feels of current trends. Even back in her early days on the Hollywood Scene, the actress knew what styles worked best on her, and those were the ones she typically stuck with.

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Alongside Friends co-star Matthew Perry, and looking every bit like the Rachel Green we know and love with her iconic layered hairstyle, Jennifer Aniston worked the Emmy’s red carpet in a classic strapless black gown with chic satin gloves. Like so many of her red carpet looks, this one is timeless.

By 1998, Jennifer Aniston was becoming notorious for her love of classic black strappy dresses and loose, wavy hair. So when the actress showed up to VH1’s Divas Live red carpet in this grey monochromatic two-piece outfit and her hair pulled back in a half-up half-down style, it was a moment.

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While we normally love to see Jennifer Aniston experimenting outside of her fashion comfort zone, we can’t say we loved her look for the 1999 Emmys. From the less-than-flattering detail on her gown to the beachy dreads in her hair, none of it seemed to work on the otherwise stunning actress.

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Finally getting a pulse on the kind of boho-styling that works for her, Jennifer Aniston glided onto the SAG Awards red carpet in 2000 wearing a simple-yet-stunning halter-style gown and flowing wavy hair in a half-up style. The look was minimalist and timeless, and oh-so-Jen.

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Redeeming herself for her Emmy’s fail in 1999, Jennifer Aniston, complete with the ultimate arm candy – hi Brad! – stepped onto the red carpet at the Emmys in 2000 wearing a stunning red strapless gown by Prada. With her hair elegantly pulled back and accessories kept to a minimum, this ranks as one of our favourite looks of all time from the actress.

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Wearing a dress that only Jennifer Aniston could pull off, the actress stepped onto the SAG Awards red carpet wearing a navy blue gown with keyhole cutout details that by all accounts, shouldn’t work, but totally did on the actress’ petite frame.

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Wearing vintage Valentino to the 2004 Golden Globe Awards, Jennifer Aniston stood out as one of the best-dressed of the night. The simple gown with its risqué cutout neckline and low back was a perfect fit for the actress, who looked confident and comfortable in her pick for the big night.

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For the premiere of her film The Break Up, Jennifer Aniston stepped out in a strapless dress that featured a ribbed-style top and nude slip skirt. The dress was fun and fresh, and worked perfectly with Jen’s easy-waves hairstyle and minimalist strappy heels.

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Following her split with Brad Pitt and new relationship with John Mayer, fans watched eagerly on Oscar night to see if there might be any friction between Jennifer Aniston and Angelina Jolie amid all the post-break up rumors. Instead, all eyes were on Jen’s choice of dress for the evening – the metallic gown fit the actress like a glove and easily ranks as one of her best red carpet moments of all time.

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While Jennifer Aniston’s hilarious speech at the Women In Film event stood out from the other speaker’s of the night, it was her showstopping metallic Prada mini dress that had the crowd buzzing.

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Giving us the style moment we never knew we needed, Jennifer Aniston rocked a one-shoulder black gown with a thigh-high slit to the 2010 Golden Globes and we are still not over it.

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Debuting her celebrity fragrance in 2011, Jennifer Aniston gave us chills when she wore an unexpected pop of colour and sported a shorter – and blonder – hairstyle for the event. We love that Aniston occasionally continues to try new things and have some fun with her red carpet style.

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Proving she’s always got a few tricks up her sleeve, Jennifer Aniston opted for a sleek pantsuit – complete with a daring neckline, of course – when she stepped out for the Critics Choice Movie Awards in 2015.

After nailing it at the same event the year before, we had high hopes for Jennifer Aniston’s Critcs Choice Movie Awards dress in 2016 – but unfortunately, the pale teal-grey Saint Laurent gown totally missed the mark. From the awkward neckline to the seemingly-poor fit and out of place seam running up the center of the dress, this one just didn’t do it for us.

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Head-to-toe Swarovski crystals, a lower-than-low neckline and a super-high slit? This could only be the show-stopping Atelier Versace gown Jennifer Aniston wore to the 2017 Vanity Fair Oscar Party.

As much as we love watching Jennifer Aniston rock the red carpet, it’s important to remember that the former Friends star is also a street style queen. While she may not sport the latest trends or take many risks with her off-duty style, she knows what works for her and manages to keep it feeling fresh and current year after year. There’s just no one that knows how to elevate a white tee, aviator sunglasses and sneakers quite like Jen.

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Looking every bit the leading lady while attending the premiere for her new film, Murder Mystery, Jennifer Aniston showed off her toned legs in a black leather mini dress that felt updated from her usual go-to styles with its belted detail and high-neck. We love Jen’s ability to stick to what she likes in fashion, while always managing to incorporate current trends and contemporary details in subtle ways.

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