Best known for her role as Rachel Green on Friends, Jennifer Aniston is a powerhouse actress who has managed to capitalize on her popularity on the mega-hit TV show and morph it into a long-lasting career with range. Just like her resume, Jennifer Aniston’s style history has come a long way. Follow along as we take you beyond the iconic hairstyle and journey through Jennifer Aniston’s style evolution.

Getty Images
1 / 20
Jennifer Aniston is a 90’s classic at NBC’s All Stars Party in 1990
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!
You won’t believe how much it costs to look like Jennifer Aniston for a year…
You won’t believe how much it costs to look like Jennifer Aniston for a year…

Getty Images
2 / 20
Jennifer Aniston forecasting future trends in 1995
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.
RELATED: Behind the scenes: amazing celebrity stylists.
RELATED: Behind the scenes: amazing celebrity stylists.

Getty Images
3 / 20
Jennifer Aniston looks flawless at the 1995 Emmy Awards
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.

Getty Images
4 / 20
Jennifer Aniston tries something new for VH1’s Divas Live in 1998
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.
YOU MAY ALSO LIKE: JLo's style evolution.
YOU MAY ALSO LIKE: JLo's style evolution.

Getty Images
5 / 20
Jennifer Aniston misses the mark at the Emmy Awards in 1999
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.
A style icon is born – check out Lady Gaga’s style evolution.
A style icon is born – check out Lady Gaga’s style evolution.

Getty Images
6 / 20
Jennifer Aniston masters the boho-vibe at the SAG Awards in 2000
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.
YOU MIGHT ALSO LIKE: 37 celebrity couples you won't believe were once together.
YOU MIGHT ALSO LIKE: 37 celebrity couples you won't believe were once together.

Getty Images
7 / 20
Jennifer Aniston in Prada at the Emmy Awards in 2000
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.
The power of love – and a great fashion sense – check out Celine Dion’s style evolution.
The power of love – and a great fashion sense – check out Celine Dion’s style evolution.

Getty Images
8 / 20
Jennifer Aniston pulls it off at the SAG Awards in 2003
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.
YOU MIGHT ALSO LIKE: Fashion fails: the worst celebrity looks of the month.
YOU MIGHT ALSO LIKE: Fashion fails: the worst celebrity looks of the month.

Getty Images
9 / 20
Jennifer Aniston in another cut-out dress at the Golden Globe Awards in 2004
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.
Read up on some fashion history with the most iconic style moments of the 20th century.
Read up on some fashion history with the most iconic style moments of the 20th century.

Getty Images
10 / 20
Jennifer Aniston goes strapless at a premiere in 2006
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.
YOU MIGHT ALSO LIKE: 14 body-positive fashion brands that are killing it.
YOU MIGHT ALSO LIKE: 14 body-positive fashion brands that are killing it.

Getty Images
11 / 20
Jennifer Aniston wows at the Academy Awards in 2009
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.
We hate to say it, but Jen makes our list of celebrities who were dumped in the worst ways possible.
We hate to say it, but Jen makes our list of celebrities who were dumped in the worst ways possible.

Getty Images
12 / 20
Jennifer Aniston shows some skin while attending Women In Film’s Crystal and Lucy Awards in 2009
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.
YOU MIGHT ALSO LIKE: 15 simple things stylish women do every day.
YOU MIGHT ALSO LIKE: 15 simple things stylish women do every day.

Getty Images
13 / 20
Jennifer Aniston rocks a higher-than-high slit to the Golden Globe Awards in 2010
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.
Now and then – these are the celebrity style makeovers you have to see to believe.
Now and then – these are the celebrity style makeovers you have to see to believe.

Getty Images
14 / 20
Jennifer Aniston debuts her fragrance in 2011
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.
RELATED: Bet you didn't know these celebs have beauty lines.
RELATED: Bet you didn't know these celebs have beauty lines.

15 / 20
85th Annual Academy Awards – Arrivals

Getty Images
16 / 20
Jennifer Aniston suits up at the Critics Choice Movie Awards in 2015
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.

Getty Images
17 / 20
Jennifer Aniston wears Saint Laurent gown to the Critics Choice Movie Awards in 2016
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.
Jennifer Aniston makes our list of celebrities who were way better off after their breakups.
Jennifer Aniston makes our list of celebrities who were way better off after their breakups.

Getty Images
18 / 20
Jennifer Aniston wears Atelier Versace to the Vanity Fair Oscar Party in 2017
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.

Getty Images
19 / 20
Jennifer Aniston is still the queen of casual-cool in Paris, France in 2017
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.
Another thing Jen is known for – making our list of the most scandalous breakups in Hollywood history…
Another thing Jen is known for – making our list of the most scandalous breakups in Hollywood history…

Getty Images
20 / 20
Jennifer Aniston shows some leg at the premiere for Murder Mystery in 2019
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.
YOU MIGHT ALSO LIKE: 20 cute dresses under $100 in Canada.
YOU MIGHT ALSO LIKE: 20 cute dresses under $100 in Canada.
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT
ADVERTISEMENT