Jennifer Aniston’s best-ever looks - from 90s slip dresses to modern red carpet gowns

Jennifer Aniston’s best ever looks really stand the test of time. These are our all-time favourites for timeless style inspo.

composite of three of jennifer aniston's best ever looks
(Image credit: Getty Images)

Jennifer Aniston's best ever looks are not easy to narrow down. With over three decades of stellar ensembles to choose from, there are hundreds of impressive style moments all deserving of appreciation.

However, there are several in particular that will always stand out. The queen of 90s fashion trends, many of our top picks come from her relaxed wardrobe era at the beginning of her career. From stacks of bangles to animal-printed handbags, Jennifer Aniston also knew a thing or two about how to accessorise back then too. But although we will always use her early looks as sources of inspiration for a trendy minimalist capsule wardrobe, her more recent picks are undoubtedly some of her best of all time.

Sticking to maxi cuts, figure-hugging fits, and perfectly tailored co-ords, Jennifer Aniston's modern style proves that even the most simple of designs can make for a killer look on her. From her jeans-and-a-shirt look at age 21 to the bias cut and mini metallic gowns she has favoured in recent years, these have to be our 32 favourite Jennifer Aniston looks of all time. 

Jennifer Aniston's best-ever looks

1. Screen Actors Guild Awards, 2020

Jennifer Aniston

(Image credit: Getty)

This stunning ivory bias-cut dress is by far one of Jennifer's best ever looks. A vintage John Galliano for Dior design that is said to have come from her own archive, it looks absolutely incredible on her. We love the lack of accessories that let the timeless and beautiful gown do the talking.

2. Critics' Choice Movie Awards, 2015

Jennifer Aniston in a red suit

(Image credit: Getty)

A trouser suit is a foolproof choice for any occasion, but this daring low-cut take by Gucci is a real standout. Red looks gorgeous on Jennifer and the body chain detail adds an edgy feel to this awards show look, cementing it as one of her most notable.

3. The Morning Show Press Conference, 2019

Jennifer Aniston wearing black wide leg trousers, t shirt and strappy heels

(Image credit: Getty)

All-black outfits are totally timeless and we love the casual edge this sleek and stylish look has. Although less statement than her red carpet ensembles, this is a perfect example of why Jennifer Aniston's sophisticated everyday style is worth paying attention to. 

4. Rachel Green LBD, 1996

Jennifer Aniston in the 90s wearing a little black dress and slingback heels

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Jennifer Aniston's 90s looks for Friends are undoubtedly some of her most iconic and this LBD couldn't be more chic. This press shot from 1996 perfectly captures her style at the time - simple accessories and a strappy dress, no doubt finished off with a pair of the best designer heels

5. Premiere of Murder Mystery 2, 2023

Jennifer Aniston wearing a silver mini dress

(Image credit: Getty)

One of her most modern looks, this mini dress by Atelier Versace is both playful and classic. Silver is another colour that suits Jennifer's skin tone beautifully, so this was always going to be a winner. Teamed with her signature strappy heels and a smokey eye, it takes monochromatic dressing to the max. 

6. The 52nd Annual Emmy Awards, 2000

Jennifer Aniston in the 90s wearing a red floor length dress

(Image credit: Getty)

The question of how to dress simple but stylish is particularly tricky to answer for formal events, but this slinky red dress nails it. Typically 90s in the best way, the strapless cut and maxi silhouette are both elegant and cheeky.

7. Vanity Fair Oscar Party, 2017

jennifer aniston at the Vanity Fair Oscar Party 2017 in a black sequin dress

(Image credit: Getty Images)

Black is a colour that Jennifer regularly wears for red carpet events and it looks gorgeous every time. Despite the simple colour palette, the deep V cut, daring leg slit, and sequinned finish elevate this gown beyond a typical slip.

8. New York, 2002

Jennifer Aniston wearing a white cami top and jeans in new york

(Image credit: Getty)

Some of Jennifer Aniston's best outfits are her off-duty ones, and this throwback photo from 2002 speaks for itself. The silk cami top and low-waisted jeans combo are the epitome of casual yet trendy Y2k fashion that she would look just as good in today.

9. 54th Annual Primetime Emmy Awards, 2002

Jennifer Aniston with wavy hair wearing a light pink gown

(Image credit: Getty)

Another early 00s look, this light pink Emmy's gown will always stick in our memory - largely thanks to the styling. The backwards draped scarf was a style staple at the time and it balances the V neck beautifully, whilst the embellishment adds a luxurious touch.

10. Picture Perfect New York Premiere, 1997

Jennifer Aniston wearing a white and gold floral midi dress

(Image credit: Getty)

Florals can be very hit or miss in formal wear, but we love this structured dress and matching 90s mini bag that only Jennifer could pull off so well. She has always been loyal to the strappy dress look, rocking it from the early 90s right up to now.

11. 9th Annual Screen Actors Guild Awards, 2003

Jennifer Aniston wearing a black maxi cutout dress

(Image credit: Getty)

Another statement black dress moment, this bold cut-out dress stays true to Jennifer's laid-back red carpet style of the early 00s. In a maxi length and up styled with a clutch bag and glitzy bangle, it does minimalism perfectly.

12. Office Christmas Party Premiere, 2016

Jennifer Aniston wearing a patchwork printed maxi dress

(Image credit: Getty)

This dress marks a departure from Jennifer's usual style and we love it. The patchwork finish is a bold choice, but one that totally paid off. Ideal for inspiring a boho capsule wardrobe, the intricate beading and muted yet varied colour palette make for a standout look.

13. 9th Annual GLAAD Media Awards, 1998

Jennifer Aniston in the 90s wearing a white midi dress

(Image credit: Getty)

Despite this being one of Jennifer Aniston's most simple looks, it is still one of our favourites. From the leopard print bag to the rounded glasses, her sophisticated style is perfectly encapsulated by the straight midi dress and sleek up-do. 

14. 85th Annual Academy Awards, 2013

Jennifer Aniston wearing a red strapless gown on the red carpet

(Image credit: Getty)

The 2010s saw Jennifer opting for bigger and more dramatic gowns on the red carpet, but the strapless cut offers a nod to her former style. This show-stopping Valentino Haute Couture number is the perfect elegant piece for the red carpet occasion. 

15. The 6th Annual Screen Actors Guild Awards, 2000

Jennifer Aniston in the 90s wearing a brown maxi dress on the red carpet

(Image credit: Getty)

Brown was a big 90s colour trend and we love Jennifer's vintage halter neck two piece in this chocolate hue. Styled with hoop earrings and a stack of bangles, it perfectly captures the feel of her laid-back 2000s wardrobe.

16. Murder Mystery 2 photocall, 2023

Jennifer Aniston wearing a champagne dress at the murder mystery 2 premiere

(Image credit: Getty)

Figure-hugging silhouettes are another favourite of Jennifer Aniston's and this Celine gown looks phenomenal on her. In a champagne colour with added sparkle, it is timelessly glamorous and made for the red carpet.

17. 21st Annual Critics' Choice Awards, 2016

Jennifer Aniston wearing a light blue gown on the red carpet

(Image credit: Getty)

We've rarely seen Jennifer in blue - apart from her off-duty denim - so this blue/grey dress from 2016 sticks out in our memory. Designed by French clothing brand, Saint Laurent, it has a floaty feminine feel that still makes a statement, thanks to the bust detailing.

18. The Good Girl Premiere, 2002

Jennifer Aniston in the 90s wearing a white tank top and blue maxi skirt

(Image credit: Getty)

We can't believe that these pared-down outfits used to be standard on the red carpet, but we love it. Worn to the premiere of indie film The Good Girl, Jennifer proved that she can even make a white tank top look effortlessly chic.

19. The Late Show with Stephen Colbert, 2019

Jennifer Aniston wearing a black strapless midi dress

(Image credit: Getty)

Combining several of Jennifer's favourite cuts, this strapless midi dress looks phenomenal on her. Photographed on the streets of New York ahead of her appearance on The Late Show with Stephen Colbert, she perfected the standout yet sophisticated look. 

20. Coney Island, 1997

Jennifer Aniston in the 90s wearing a printed skirt, yellow cardigan and bucket hat

(Image credit: Getty)

Captured on set in Coney Island in 1997, this outfit has a girl-next-door vibe that we love seeing on Jennifer. From the bucket hat to the statement mini skirt, it has a 70s hippie feel that we will be taking inspiration from for holiday and summer outfit ideas.

21. New York, 2023

Jennifer Aniston wearing a beige dress and coat

(Image credit: Getty)

Neutral pieces make the best winter coats and Jennifer proves it with this look. The beige knee-length dress and sleek long jacket work harmoniously together, ideal for the New York City weather, whilst the brown sunglasses add a cool edge that makes this one of her best ensembles. 

22. VH-1 Divas Live Concert, 1998

Jennifer Aniston in the 90s wearing a long sleeve madi dress

(Image credit: Getty)

We love how classically 90s this co-ord is, so it had to make this roundup. You would never spot a look like this on a red carpet today, but Jennifer carried it perfectly back in '98. True to style with barely-there sandals and a black clutch, it is another signature JenAn ensemble.

23. Zoolander 2 World Premiere, 2016

Jennifer Aniston wearing a floor length maroon dress

(Image credit: Getty)

This Galvan corset dress captures the quiet luxury look, thanks to its sophisticated maroon hue. The column style looks wonderful on Jennifer and the squared-off neckline and small V-cut work to add shape to the look. A truly timeless dress, it will always be one of our favourites.

24. Six Days & Seven Nights Premiere, 1998

Jennifer Aniston wearing jeans and a sheer black top in the 90s

(Image credit: Getty)

The queen of mom jeans outfits, Jennifer Aniston has always been a source of inspiration for trendy denim looks. Although it's hard to believe this is a red carpet outfit, we love what it says about her personal style early on in her career - relaxed yet on trend.

25. Los Angeles, 2019

Jennifer Aniston wearing white jeans and a blazer

(Image credit: Getty)

For further jeans inspo, this black and white outfit has a more modern and sophisticated feel. Sporting an oversized blazer, designer crossbody bag, and pointed toe boots, Jennifer demonstrates how you can dress up simple pieces to achieve a fashion-forward everyday look.

26. 51st Annual Emmy Awards, 1999

Jennifer Aniston wearing an embellished brown dress

(Image credit: Getty)

The embellished bodice of this dress deserves an honourable mention. A standout amongst her other 90s looks, it balances beautifully with the simple skirt, drawing the eye upwards. Reinventing the tank dress, it is a truly memorable look of hers.

27. New York, 2022

Jennifer Aniston wearing a black long sleeve co-ord

(Image credit: Getty)

Yet another chic co-ord, this shirt and suit trouser combination demonstrates how Jennifer takes classic silhouettes and reinvents them for her signtaure style. With a cropped cut, the shirt works to highlight the high-waisted trousers and elongate her frame. 

28. 7th Annual People's Choice Awards, 2001

Jennifer Aniston with a bob wearing a black satin gown

(Image credit: Getty)

One final black gown had to make this list, and it's only right to go back to one of Jennifer's first. This maxi satin dress is one of the most timeless pieces she has worn, but we love how the side-parted bob and statement cross necklace place it firmly in the early 00s and add a grungy feel to the look.

29. Vanity Fair Post Oscar Party, 2015

Jennifer Aniston wearing a champagne dress at the vanity fair party

(Image credit: Getty)

Made up of body-contouring panels and a playful sheer fabric, this strapless gown is one of our favourite ever Vanity Fair party looks. Balancing between chic and daring, it takes one of Jennifer's signature colours and reinvents it with a combination of textures.

30. Cake Los Angeles Premiere, 2015

Jennifer Aniston wearing a white bow top and mini skirt

(Image credit: Getty)

This look is unlike any others we've seen Jennifer Aniston wear, which is why we love it. With a preppy feel, thanks to the bow detail neckline and a simple yet eye-catching printed mini skirt, it is a sweet ensemble that we'd love to see her in again.

31. Life Of Crime Premiere, 2013

Jennifer Aniston wearing a blue midi strapless dress

(Image credit: Getty)

A signature Vivienne Westwood corset dress, this is another look that experiments with Jennifer's edgier side. The draped skirt and fitted bodice look stunning on her figure, whilst the blue hue works wonders with her blonde hair. 

32. NBC Stars Party, 1990

young Jennifer Aniston wearing jeans and a grey shirt

(Image credit: Getty)

A true throwback picture, this image of a 21-year-old Jennifer Aniston is one of our favourites. The simple grey shirt and jeans combo may not be as standout as her red carpet gowns, but we love her cool, youthful look that this picture highlights - a sign of her impeccable style to come.

Amelia Yeomans
Senior writer

Amelia joined woman&home in 2022 after graduating with an MA in Magazine Journalism from City University and she is now a senior fashion and beauty writer. She began building her career as a lifestyle journalist after completing a fashion journalism course at the Condé Nast College of Fashion & Design in 2019, writing for a variety of titles including OK!, New!, and Notion on topics such as sustainable fashion and entertainment.