Jennifer Aniston’s Style Throughout The Years

3 years ago

1. Jen at NBC’s All Stars Party - 1990

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A very young Jennifer Anniston, looking very fashionable with a boxy blouse tucked into her jeans and the obligatory chunky looped belt to pull it all together. Big hair was so 'in' during this decade and Miss A did her best to expand the texture, for that fluffy appearance!

2. Miss Aniston at the Emmy Awards - 1995

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Here she is alongside her co-star, Matthew Perry. Most noticeable is the layered hair style which became iconic She is pictured working the red carpet in a strapless black gown with chic satin gloves Even though this was 1995, the classic style would not look out of place today.

3. Forecasting Future Trends - 1995

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Jennifer Aniston ALWAYS looks flawless and she didn't disappoint in this satin midi dress, strappy heels and hair styled in beachy waves. She was giving us all the feels of current trends from the mid 90s when satin was huge. An unforgiving fabric for some but not for Jennifer, with her amazing slender figure.

4. Something New for VH1’s Divas Live - 1998

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By 1998, Jennifer Aniston was becoming notorious for her love of classic black strappy dresses and free flowing wavy hair. It was a surprise, then, to see the actress turn up to VH1’s Divas Live event in a grey monochromatic 2-piece outfit with her hair pulled back in a half-up half-down style.

5. Some Say Not Her Best Look At The Emmys - 1999

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While we normally love to see Jennifer Aniston experimenting outside of her comfort zone, fashion wise, some critics weren't sure of her choice for the 1999 Emmys. They thought the detail on her gown was unflattering (really!) and the weren't a fan of the beachy dreads in her hair.

6. The Lady Wear Prada With Brad At Emmys - 2000

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Redeeming herself for her Emmy’s fail in 1999, Jennifer Aniston, complete with her then husband Brad Pitt, worked the red carpet at the Emmys in 2000. She wore a stunning red strapless gown by Prada and her hair was elegantly pulled back. Minimal accessories were perfect to create this image of beauty

7. Jennifer Goes Boho At SAG Awards - 2000

Image source Getty ImagesNot like Jennifer to go boho but she took the plunge and glided on to the red carpet at the SAG Awards in 2000. The simple halter dress looked great although practically everything she ever wore made us a tad jealous. Her lightly curled hair in a half-up completed the vision.

8. Creating A Stir At The SAG Awards - 2003

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Wearing a dress that only Jennifer Aniston could pull off, the actress stepped on to the SAG Awards red carpet in a gorgeous navy blue gown with keyhole cut-out details that could look gross on many women but totally worked on her petite frame. Her hair was straightened and the colour was spot on.

9. Very Revealing At The Golden Globes - 2004

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Wearing vintage Valentino to the 2004 Golden Globe Awards, Jennifer Aniston took the title, from the fashion police, as one of the best-dressed of the evening. The simple gown with its risqué neckline, not showing too much and low back was a perfect fit for the actress.

10. Strapless Number For A Premiere - 2006

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For the premiere of the movie she starred in, 'The Break Up', Jennifer Aniston stepped out in a strapless dress featuring a ribbed-style top and nude slip skirt. The dress was fresh and fun, working perfectly with Jen’s loose-waves hairstyle and minimalist strappy heels.

11. Leaving Little To The Imagination At Women In Film’s Crystal And Lucy Awards - 2009

Almost popping out of her show-stopping mini metallic dress designed by Prada, Jennifer Aniston’s hilarious speech at the Women In Film event was miles ahead of the other speakers of the night. She oozed confidence, knowing she looked the business and well as working the crowd.

12. Wow Wow Wow At The Academy Awards - 2009

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Following her split with Brad Pitt and now in a relationship with John Mayer, fans watched eagerly on Oscar night to see if there was any friction between Jennifer Aniston and Angelina Jolie because of all the rumours floating around Hollywood. Instead, all eyes were fixed on Jen’s gown which fit like a glove. The fashion magazines raved about it! .

13. A Higher-Than-High Split At Golden Globes - 2010

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Giving us the style moment we never knew we needed! Jennifer Aniston totally rocked this one-shoulder black gown with a higher than high thigh slit. She was attending the 2010 Golden Globes and worked that carpet to capacity. This image made the front pages of so many publications.

14. Looking Cute Presenting Award At Golden Globes - 2011

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When you are asked to present an award at the Golden Globes, all eyes are on you and you want to draw the audience in. After a huge round of applause on her entrance, Jen threw out a few funny lines but nothing funny about the Valentino gown and 5 inch heels!

15. Business Woman Debuts Her Fragrance - 2011

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Debuting her celebrity fragrance in 2011, Jennifer Aniston gave us chills when she wore an unexpected choice of colour by plumping for orange. Of course, it suited her down to the ground, as did the shorter and blonder hairstyle. As always, she looked a million dollars! .

16. 'She's Funny That Way' On Set - 2014

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During filming of 'She's Funny That Way', Jennifer Aniston was 'papped' on her way to the studio. Totally unruffled, she was dressed casually, but perfectly as usual, in a striped tee-shirt, cut off shorts and high wedges, showing off her slender pins. Even the script in her hand and bottle of water looked like a glamorous photograph.

17. Suited And Booted At Critics Choice Movie Awards - 2015

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Proving she’s always got a few tricks up her sleeve to keep us wanting more, Jennifer Aniston opted for a sleek trouser suit, complete with a very daring neckline. Hope she had some body tape on there! The occasion was the Critics Choice Movie Awards in 2015.

18. Wearing Saint Laurent At Critics Choice Awards - 2016

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After nailing it at the same event the previous year, there were high hopes for Jennifer Aniston’s Critics Choice Movie Awards dress in 2016. Some said it didn't quite cut it with the pale teal-grey Saint Laurent gown. From the neckline to the seemingly-poor fit and out of place seam running up the centre of the dress, this one didn't have the usual wow factor.

19. Scrubbing Up Well In Atelier Versace Vanity Fair Oscar Party - 2017

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Head to toe in Swarovski crystals, a lower-than-low neckline and a super-high slit? This was the ultimate show-stopper that other actresses wished they could have worn and looked like her! The Atelier Versace gown Jennifer Aniston stunned in was at the 2017 Vanity Fair Oscar Party.

20. Leather Look At Premiere Of 'The Leftovers' in L.A. - 2017

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Jennifer Aniston turned up at the Los Angeles Premiere of 'The Leftovers' Season 3 on April 4, 2017 in a leather one-shoulder mini dress from Brandon Maxwell’s Fall/Winter collection 2017. The outfit was completed with high strappy black heels. Her beau at the event was new love at the time, Justin Theroux.

21. Still Queen Of Casual-Cool in Paris - 2017

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The actress, a street style queen, may not sport the latest trends or take too many risks with her off-duty style but she sure 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 Jennifer!

22. Going Geometric At Gala Tribute To George Clooney - 2018

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Here we see Jennifer Aniston wearing a geometric black gown with a white clutch bag and sandals at the American Film Institute’s 46th Life Achievement Award Gala Tribute To George Clooney in 2018. The slight crimping of her hair was just enough to set the scene.

23. Sneaking Around At W.E. Day, California - 2018

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Jennifer Aniston keeps it very casual in a black blazer, cuffed jeans and white sneakers at WE Day California on April 19, 2018. A fan of the narrow jeans, she has been shown to dress them up or go for a more relaxed feel, still looking elegant either way.

24. Glowing At The Golden Globes 2018

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There is a simple reason why Miss Aniston always turns to black when it comes to major events - it works every time! Never shy to show a bit of leg, Jennifer was not shy in flaunting her figure, the sign of a confident woman. Interestingly, she always tended to look sexier after a relationship break up - a sign of what her ex partners were missing.

25. Jennifer Wears Stella McCartney At L.A. Premiere - 2018

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Jennifer simply shimmered in this sequinned little back dress by Stella McCartney. She teamed it with minimal sandals at the Los Angeles Premiere in December 2018 of 'Dumplin', the Netflix movie. Her hair was subtly highlighted and she looked so glamorous.

26. If You've Got It, Flaunt It At 'Murder Mystery' Premiere 2019

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Looking every bit the leading lady while attending the premiere of her movie 'Murder Mystery', Jennifer Aniston showed off her toned legs in a black leather mini dress that felt totally on trend. The delicate strappy sandals with front bows softened the whole look.

27. Preview of 'The Morning Show' in New York City - 2019

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Jen Aniston certainly looked the part, is seen wearing a Maison Margiela dress, Rick Owens blazer and black high heeled boots, to Apple’s 'The Morning Show. There was an exclusive sneak peek preview screening at the Paley Centre for Media in New York City on October 29, 2019.

28. Very Business Like In Pin Stripes At Variety’s Power Of Women Lunch - 2019

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Jennifer Aniston looked amazing in this low key pinstripe dress and chic black patent pumps. She was attending the Variety’s Power of Women luncheon event in Los Angeles in December 2019. Her face make up was kept minimum, looking very natural.

29. Scoop Neck Gown At 6th Annual SAG Awards - 2020

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The actress attended the 6th Annual SAG Awards in January 2020. She chose to wear a scoop neck cream gown falling into a fish tail, showing her curves in all the right places! If Jennifer wasn't stunning in a LBD she often chose to wear white or cream which she could carry off perfectly.

30. Looking Summery On Way To 'Kimmel' Show - 2021

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Jen was snapped in September 2021 wearing a very summery strappy maxi dress. Her accessories were a cream bucket bag and very high black sandal heels. Her layered hairstyle was a little longer than usual but, of course, she looked as incredible as ever.

Jennifer Aniston’s Style Throughout The Years

1. Jen at NBC’s All Stars Party - 1990

2. Miss Aniston at the Emmy Awards - 1995

3. Forecasting Future Trends - 1995

4. Something New for VH1’s Divas Live - 1998

5. Some Say Not Her Best Look At The Emmys - 1999

6. The Lady Wear Prada With Brad At Emmys - 2000

7. Jennifer Goes Boho At SAG Awards - 2000

8. Creating A Stir At The SAG Awards - 2003

9. Very Revealing At The Golden Globes - 2004

10. Strapless Number For A Premiere - 2006

11. Leaving Little To The Imagination At Women In Film’s Crystal And Lucy Awards - 2009

12. Wow Wow Wow At The Academy Awards - 2009

13. A Higher-Than-High Split At Golden Globes - 2010

14. Looking Cute Presenting Award At Golden Globes - 2011

15. Business Woman Debuts Her Fragrance - 2011

16. 'She's Funny That Way' On Set - 2014

17. Suited And Booted At Critics Choice Movie Awards - 2015

18. Wearing Saint Laurent At Critics Choice Awards - 2016

19. Scrubbing Up Well In Atelier Versace Vanity Fair Oscar Party - 2017

20. Leather Look At Premiere Of 'The Leftovers' in L.A. - 2017

21. Still Queen Of Casual-Cool in Paris - 2017

22. Going Geometric At Gala Tribute To George Clooney - 2018

23. Sneaking Around At W.E. Day, California - 2018

24. Glowing At The Golden Globes 2018

25. Jennifer Wears Stella McCartney At L.A. Premiere - 2018

26. If You've Got It, Flaunt It At 'Murder Mystery' Premiere 2019

27. Preview of 'The Morning Show' in New York City - 2019

28. Very Business Like In Pin Stripes At Variety’s Power Of Women Lunch - 2019

29. Scoop Neck Gown At 6th Annual SAG Awards - 2020

30. Looking Summery On Way To 'Kimmel' Show - 2021

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