Jennifer Aniston has been a style icon since she burst onto the scene in the early ’90s. There was even a hairstyle named after her character in Friends. If you wanted to be cool in 1995, you got the Rachel haircut. Since starring on Friends, Jen has gone on to star in a bunch of movies and romantic comedies.
We’ve put together a list of all of her best looks over the years. Keep reading to learn more about her style evolution.
Little Black Dress
Nobody loves a little black dress more than Jennifer Aniston. This look is somehow both very ’90s and completely timeless. This is Jennifer Aniston at the height of her career. Friends was a smash hit, she was making more money than she knows what to do with, and she was rocking the hairstyle that changed the world.
She chose to keep her look simple, because no dress can compete with all of that success.
Back At It Again With The LBD
The satin finish of this little black dress makes it look a bit fancier than your average spaghetti strap number. She’s also bringing a bit of that ’80s shine into the ’90s. There’s something about a simple black dress like that that’s just undeniably sexy.
Jen looks like she’s going to the most expensive prom you’ve ever seen. All she needs now is a white corsage and she’s good to go.
These women all look so perfectly ’90s, it’s making me so nostalgic. I think these outfits would still be fashionable today, but there’s something about the fit of them— how oversized they are— that just takes me back to a simpler time.
I love what Lisa Kudrow and Courteney Cox are wearing in this photo, but can somebody please find me Jennifer Aniston’s whole outfit? She makes turtlenecks look so good.
A Leather Queen
In this photo, Jennifer looks like the yin to Brad Pitt’s yang. Or is Jen the yang and Brad the yin? We may never know… I like that they’re both wearing leather jackets but that Jen’s is a light tan and Brad’s is a classic black.
They look like the perfect pair— if they only knew what was to come. At least they were cute while it lasted. Why did you have to cheat, Brad?
Show A Little Skin
There they are! The friends! I mean, the entire main cast of the show Friends. It must be winter because they’re all wearing dark clothes, although what Jen’s wearing doesn’t look all that suitable for winter. Maybe showing that much skin is okay for winter in LA.
Rachel couldn’t get away with wearing a shirt that revealing in January in New York, but she looks absolutely stunning in this photo.
Old Hollywood Glam
So far we’ve only seen Jen in dark clothes. It’s kind of refreshing to see her in something light and ethereal. The details on this dress are just gorgeous, and her loose, carefree waves match the vibe of the outfit.
I don’t know what’s going on with Brad Pitt’s hair, though. Short hair is definitely a better look for him. I’d like to see Jen in this super pale blush more often.
A Shirt Or A Dress?
So, I think this outfit is most likely a fashion misstep. What do you think? I’m not into the long shirt-dress over pants thing. Like, is it a shirt or a dress? Make up your mind.
I kind of like the dress on its own, but it without the pants it could almost look like lingerie. It’s a delicate balance, but I don’t think Jen struck it here. Nothing about this look screams high fashion.
A Golden Evening
Jennifer Aniston looks like a real life mermaid in this white dress with gold detailing. Brad’s sorted out his hair and they look pretty happy together. I’m not sure about the cut of this dress, though. I don’t think the empire waist is doing anything for her figure (and Jennifer Aniston has a near perfect figure).
It’s just not my cup of tea, but her hair and makeup look radiant.
The ’90s are over, people. We’ve made it into the 2000s. This is a photo of Brad Pitt and Jennifer Aniston at the premiere of The Bourne Identity in 2002. I know Jen’s bohemian looking shirt isn’t really high fashion, but I have to say that I’m super into it. I think it suits her body really well, and If I saw it in a store today I would definitely try it on.
I’m not sure if it fits the occasion, but I don’t really care because Jen looks great.
A Timeless Classic
We’re deeper into the 2000s now, and Jen is at the premiere of He’s Just Not That Into You at the Grauman’s Chinese Theatre. All the other ladies in this photo are wearing bright colors, interesting textures, and bold patterns.
Not Jen, though. She’s sticking to a classic black pantsuit with some eye-catching gold jewelry. She has her hair tied back and she looks like she’s all business. She looks like a woman who wants to be taken seriously.
Shine Bright Like A Diamond
This is a photo of Jennifer Aniston arriving to the premiere of Love Happens at the Mann’s Village Theatre in 2009. The usually serious and structured Jen has opted for a more celebratory look with this head to hip sparkly number.
Do famous people just spend all their time going to movie premieres, because if that’s the case, sign me up. I love the long sleeves on this dress; it really balance out her bare legs.
Back To Basics
Jen looked like a woman on a mission at the Los Angeles premiere of The Switch in 2010. Her tight blush satin top and simple black skirt are very office chic.
Juliette Lewis has definitely gone all out. Her dress looks like a literal party and her blue hair looks soft and edgy at the same time. Jen doesn’t take style risks like Juliette, but she knows what works on her body and she knows how to rock a red carpet.
A Need For Tweed
Jennifer Aniston wore a simple tweed dress to the Daily Show with Jon Stewart on August 19th, 2010. This dress definitely fits Jen’s aesthetic and it’s doing all kinds of good things for her figure.
Jen’s makeup is understated as usual, but that look has been working for her since the early ’90s. Jen usually wears pretty casual outfits when she appears on late night TV, but she definitely stepped it up a notch for Jon Stewart.
A Real Life Bounty Hunter
Jen picked a looser, more flowy outfit for the premiere of Bounty Hunter in New York City. The shoulder cut out in this dress almost makes it look like she was just out on the town hunting bounty. I’m not saying it looks ripped, but I’m also not not saying that it looks ripped…
I don’t hate this look, but I don’t love it either. It’s just kind of there, which is enough, I guess.
Give The Men What They Want
Jennifer Aniston accepted the Decade of Hotness award onstage during Spike TV’s 5th annual Guy’s Choice Awards in 2011. If you’re going to accept an award literally granted by the male gaze, why not do it in a slinky little black dress?
This dress reminds me of the early days of Jennifer Aniston. She’s 42 years old in this picture and she doesn’t look a day over 30. She definitely deserved that award.
In June of 2012, Jennifer Aniston attended the 40th AFI Lifetime Achievement Award honoring Shirley MacLaine in Culver City, California. We haven’t really seen Jen in a dress this bright and white before, but she definitely makes the color look good.
This dress could probably use a bit more structure, but I’m just being nitpicky. I think the cut and color of this dress are perfect for Jen. She looks like a tanned goddess.
Black And White And Jen All Over
Jen showed up to the premiere of Wanderlust in this highly structured black and white outfit. I’m usually not a huge fan of peplums, but Jen managed to pull this one off.
It seems like Jen is really into wearing black and white, whether she’s wearing all black, all white, or some combination of the two shades. This dress does look a bit too businessy for the occasion, but I think Jen can be businessy if she wants to be.
He Wasn’t Playing Around
Um, is this the best engagement ring of all time? That is an eight carat diamond, which is absolutely insane. I didn’t even know that eight carat diamonds existed. When she was first spotted wearing the ring, Jen said, "It’s a rock, I know. He rocked it up. It took me a while to get used to it. I’m not a diamond girl," she added. I’m more Indian jewelry and stuff."
Justin Theroux did a fantastic job on the engagement. If only the marriage had been as shiny.
Fabulous In Floral
Jen showed up to the London premiere of We’re The Millers in this playful floral dress. We haven’t really seen Jen wear this much color before. It seems like she’s taking a step out of her comfort zone here, but then again, this does look like a daytime event. Maybe she wears brighter clothes in the daytime?
Her hair looks great in this picture. All the highlights and lowlights are really working for her.
Jen walked the red carpet for Life of Crime at Roy Thompson Hall in Toronto in this light greyish blue dress. The silhouette of the dress is very Jen Aniston, and I especially appreciate that she chose to wear a color that isn’t black or white. It’s not a bright color, but it’s a color and I appreciate that.
The blue in the dress definitely complements her blue eyes. She should probably wear blue more often.
Lady In Red
Well, ask and you shall receive. I said I wanted color, and Jen delivered a whole lot of color. Jen arrived at the 2013 Oscars in this stunning floor length red dress. She paired it with a red clutch, some sparkly jewelry, and a handsome man. Justin Theroux looks pretty dapper in his tuxedo.
The red that Jen’s wearing is a bit more orange-toned than the red carpet. Do you think she clashes with it a bit?
A Perfect Print
Jennifer Aniston attended her own Hollywood Star of Fame ceremony wearing a red, white, and blue print. Come to think of it, Jen, Adam Sandler, and Malin Akerman kind of look patriotic all stood together like that.
The cut of this dress is perfect on Jen. It’a age appropriate and modest without being boring or old looking. It’s a perfect daytime look for an exciting occasion. Also, she kind of looks overdressed standing next to Sandler.
Playing With Texture
Jen’s arms were on display in this little black number that’s doing more than meets the eye. This picture is from HBO’s post Golden Globe Awards party at The Beverly Hilton Hotel on January 11th, 2015.
This little black dress has a high slit, a textured top, a high waist, and a simple solid skirt. Jen seems to be a fan of high necklines. This halter style dress looks gorgeous on her.
Taking A Plunge With Her Outfit
Just when I say that Jen loves high necklines she shows up to the 21st Annual Screen Actors Guild Award in this plunging subtly patterned dress. I think this is my favorite thing that Jen’s ever worn. It has a ’90s vibe, but it’s still very at home at this 2015 event.
This dress does look like a wardrobe malfunction waiting to happen, though. I wonder how much boob tape she’s wearing with this outfit.
The Year Of The Plunge
It seems like Jen favored high necklines for most of her career, and then 2015 hit and she was all about the plunge. I absolutely love this deep red pantsuit. If you’re going to wear a pantsuit, this is definitely the way to do it.
Jen and Justin looked so happy at the 20th annual Critics’ Choice Movie Awards at the Hollywood Palladium. I miss this relationship so much.
Shimmer All Over
2015 was quite a year for Jennifer Aniston. Here she is at the Vanity Fair Oscar Party hosted by Graydon Carter at Wallis Annenberg Center for the Performing Arts in February. I think I like this dress even better than her long red dress.
It’s a beautiful champagne color, it’s sparkly all over, and it has some subtle but interesting detailing along the bodice. Also, look at that rock on her left hand!
Back To Black
Jen went back to her roots in 2016 with this ruffled black (with some white squares) dress. She looks like she’s ready to dance the flamenco at the Giffoni Film Festival in Giffoni Valle Piana, Italy.
Those red shoes are to die for, and they go so perfectly with this outfit. If you’re planning on going to Italy in the summertime, this is exactly what you should wear while you’re there.
Simple Yet Sophisticated
Jen was spotted on the streets of Manhattan in September 2016 wearing this very simple white blouse and jeans combo, but wait, is that a Gucci belt? Of course it’s a Gucci belt. Jen Aniston probably has like ten of those.
I really like this look on her. It’s very New York chic. Also, the red garage in the background makes this look like an editorial shot. Justin’s not looking too shabby either.
Jen went back to black at the 2017 Vanity Fair Oscar Party. This textured black dress with a plunging neckline seems like a perfect combination of all the styles Jen has worn over the years. Her makeup is neutral, as usual, her hair is down and straight, and she looks very much like herself.
She’s come a long way since the days of Friends, but I don’t think I’ve ever loved another Jen Aniston character as much as I loved Rachel Green.
Short And Sweet
Jennifer Aniston isn’t showing any signs of slowing down any time soon. Here she is at the premiere of her new Netflix show, Dumplin’ on December 6th, 2018. This short black dress is shiny, flirty, and fun. Her hair looks great, she’s rocking a pink lip, and she looks absolutely amazing for a woman who’s almost 50 years old.
I mean, forget age, she looks amazing period. Who else is watching Dumplin’ this weekend?
Airplane Casual at LAX
When they fly the skies, celebrities tend to look a bit more put together than the rest of us. Here Jennifer Aniston is pictured in LAX, looking comfortable and casual. What’s perfect about Aniston’s outfit choice is that she can basically touch down anywhere and fit right in.
She layered some classic pieces together to easily be able to adjust to different temperatures. You’ve got to love her strappy wedges and the pop of color her aqua necklace adds.
Keeping It Low-Key
While Aniston can pick some low-key pieces out for herself, there’s no hiding from the public. Ever. Even when she dresses down to the basics, she’s still stunning and people can’t help but take notice.
Here she is in New York, meeting up with her beau at the time, Justin Theroux. Jen threw on a casual brown hat to possibly cover her face from the paps, but that won’t deter them.
Little Black Wrap Dress
When Aniston appeared at the premiere of Mothers Day at the TCL Chinese Theatre in Hollywood, she dressed to impress. This piece puts a twist on the little black dress, flaunting her toned legs with a stylish wrap cut.
We love that this dress doubles as a power suit with the suit-like sleeves and low cut neckline. She’s dressed like a knock out who’s ready to take care of business.
When Jen and Justin attended the Zoolander 2 world premiere in New York City, Aniston appeared on the purple carpet in this stunning number. The floor-length dress is an absolute winner, as Jen proves she doesn’t have to show off her killer legs at every appearance.
The color and beautifully fitting fabric bring sleek style without going over the top. The cut also offers just enough va-va-voom, don’t you think?
Aniston’s Semi-Hidden Tattoo
Did you realize that Jen had a tattoo? It’s true! The actress has ink on the inside of her foot. It’s script that reads “Norman” which is an ode to her dog. Aniston revealed that it’s also her “favorite word.”
After she got the new ink she alerted the Twittersphere, posting a photo of her new ink after leaving the tattoo parlor, captioning it, “look what I did last night.”
We Love This Look
What’s not to love about this look? Jennifer Aniston wore this stunning dress when she attended the 21st Annual Critics’ Choice Awards in Santa Monica in 2016. The delicate, lightweight fabric flatters her fit figure like a dream. Why can’t we all look this good?
We love the smokey eye makeup and soft sparkly of the straps on her dress. She was rocking a dangerously high dress slit that night!
The Perfect Fit
It can be difficult to find a formal dress with just the right cut and our jaws are dropping with this one. Similar to the light blue-silver on the previous slide, Jen does it again with this sleek gown worn at the Life of Crime premiere in Toronto.
With her hair down, it takes a glance or two to see that the dress is in fact strapless, and perfectly contours and stays in place. How elegant!
Flirty and Fun
While she’s often spotted in basic colors, this girl loves a good print. When she stepped out in London, England for the European premiere of We’re The Millers, Aniston decided to wear a fun and flirty outfit.
This knee-high dress is designed with a layered ruffle and volume, something we don’t always see Aniston wearing, but she completely pulls it off. Sometimes you just have to pull out a fun outfit for a night.
Everyone loves a good lounging outfit for summer, and Aniston is no different. When it’s hot out you’ve got to make sure to beat the heat with a cute get-up. Here she pairs a simple blue and white top with cut-off jean shorts.
We love the strappy wedge sandals that she’s seen stepping out of the car with in the first image. It seems that she got even more casual later, opting for simple flip flops. We love it.
Red Gown, Wow
It isn’t often that you see Jen in a color as bright as this brilliant red gown, but wow, can she pull it off. When you attend the Oscars and the after-parties, you’ve got to go big. And while everyone expected Aniston to look absolutely stunning, they probably didn’t expect to see her in this red.
The strapless gown has a gorgeous train and is completely eye-catching. There’s no way Justin could look away!