Quick Links

Known by millions as Rachel in the American sitcom, Friends, Jennifer Aniston was tripping the light long before this favorite US show captured audiences worldwide. In fact, her career began with 1993's, Leprechaun, but her breakthrough came with the sitcom, Friends. It only ran for a decade, but it served to transfer Jennifer into a household name. Movies have been coming thick and fast ever since the show ended in 2004. She is a popular choice for directors looking for female comedy and romantic actresses. Recent hits include Horrible Bosses, in 2011, We're the Millers in 2013, and Cake in 2014.

In 2012, she received the ultimate acting accolade, a star on the Hollywood Walk of Fame. However, it's not just her acting career that has got her noticed. She has had some pretty famous men in her life. Brad Pitt and Justin Theroux, to name only two. Her natural style is also something for which she is often making the news. She is often written about with regards to her natural beauty and is someone that many modern women try to emulate.

The 49-year-old actress and businesswoman is, without a doubt, a cherished celebrity and a respected woman. Jennifer's high moral standards even reflect her sense of style; and to make it better for all the single guys out there, Jennifer is no longer in a whirlwind relationship with Justin Theroux. Well, it may be a challenging period for both parties, but this shall pass as well. Now, get your daily dose of fashion inspiration by clicking through 20 of Jen's best looks ever.

Jen Did Not Disappoint At the 2015 Oscars

Style has not been something Jennifer has had to work at. In fact, it seems as though it comes to her quite effortlessly. In a recent interview with Fashionista, the 49-year-old Cake actress hinted that she actually loves such minimalistic approaches to fashion.

"I feel like if you're wearing a gown with glitter, and you want to have beachy, natural hair, it sort of goes against that." The actress adds, "So that’s sort of my main thing, being me. Being comfortable."

Generally, the outfits she usually wears are designed by some of the top names in the fashion industry. But whether it's Versace, Saint Laurent or Valentino, Jen wears them elegantly and comfortably. During an interview with the StyleList, Jen’s stylist, Chris McMillan, finally spilled the beans about her picture-perfect red carpet looks, like the one you’re looking at right now.

"The keyword for the night is natural," Chris revealed. “Jen's a California girl. She wants to be herself and rock that natural look on the red carpet." Well, by the look of things, they’ve achieved just that. Indeed, this champagne one-shoulder beaded gown, beautifully designed by Versace, is one of her best looks so far.

Jennifer Stole The Show In Her Gorgeous Valentino Gown

Another fabulous look comes from the 2013 Oscars, where the world saw her wearing a Grace Kelly-inspired ball gown in striking red. It was designed by Maria Grazia Chiuri and Pierpaolo Piccioli, the creative directors behind Jennifer's gorgeous, Valentino Haute Couture ball gown.

"Jennifer looks like a modern-day Grace Kelly, said Maria and Pierpaolo. We love how she wears everything with an innate naturalness."

There was nothing fancy to take away the attention from the flowing dress, which Jennifer coupled with vintage jewelry and Ferragamo clutch. Well, she might've rocked some flashy jewelry too, but, somehow, they remained understated.

Her makeup was minimal, her hair amazing, and her slight tan gave her a nice glow. The stunning gown was quite a departure from the usual little black number that Jen seems to prefer for red carpet events, but she still turned a few eyes. Indeed, onlookers and the general public were just mesmerized by her elegance and grace. This lady just loves high-end fashion brands and this gorgeously red gown, designed by Maria Grazia and Pierpaolo Piccioli, is the just the perfect example of that.

Jen Definitely Knows How To Work This Little Black Dress!

Another outfit that has stood out from all the others is the leather little black dress that she wore to Justin Theroux's premiere of his latest TV series, The Leftovers.

While it is just another variation on a theme, this off-the-shoulder creation showed off her figure to perfection. The dress was designed by Brandon Maxwell, Lady Gaga's favorite designer and stylist.

As you'd expect from such a designer, the dress was a little risque, but perfectly matched the smart black suit her ex-husband had chosen to wear. Her hair was very natural, merely loose with tousled waves, and the only jewelry items she wore were a pair of gold hoop earrings. Her makeup was also understated, allowing the glow of her tanned skin to make the statement. Jennifer is well-known for her excellent choice in red carpet outfits, and a fond favorite of hers is the little black number. With this outfit, however, she took it to a whole new level. Well, the beautiful era of Jennifer and Justin may be over, but it doesn’t mean that Jen has cried her eyes out because of it. Besides, she doesn’t really need to.

Jen’s Fab Versace Gown Was A Moment To Capture

Atelier Versace designed this beaded elegance for the charming Friends star for the 2017 Oscars. Designed to accentuate her natural curves, it must’ve taken the designers team over 300 hours to add the beads to this dress. Undoubtedly, it just fits Jennifer like a glove, and little else was needed to complete the red carpet look. She might not have been in line for any nominations in the film department, but her outfit definitely turned a few heads. As one of the presenters at the award ceremony, Jennifer looked gorgeous in her beaded black dress with a slit going up her leg. Her hairstyle was, once again, very casual, but still beautiful and her makeup not too overpowering. No bling was necessary as the dress said it all.

Finally, when you couple that with her natural Rachel-inspired hairstyle, and minimal makeup, and it's no wonder that she’s always on the cover pages of the glossy magazines.

Over the years, we’ve noticed this lovely tendency in Jenn’s wardrobe. This woman just loves being as natural as possible, and that's a great feature about her. Her reputation of an equally talented and beautiful actress means that there is no end of designers who’d love her to walk around in their glorious gowns.

Jen Wore A Deceptively Simple But Mega Charming Dress By Donna Karan

Frankly, this is something that can be said about many of her elegant attire— whether she's attending red carpet events or just nipping to the shops, Jen's styling is always on point.  In 2010, she showed up in a super charming dress designed by Donna Karan, proving how impeccable Jen's sense of style is.

Arriving at the premiere of The Bounty Hunter, Aniston just amazed the audience with her elegant gown and natural beauty.  The color was nude, which made the dress look quite unpretentious; however, it looked great on Jennifer.

Her elegant attire was indeed a delicate piece of art made from a silk jersey material. To finish off the fabulous look, Jennifer opted for a dash of elegance and shimmer, provided by her Salvatore Ferragamo purse and Fred Leighton jewelry. Moving onto her hairstyle again, Aniston rocked her signature layered and tousled look, while strappy sandals completed the dress. As lovely as it was, the flowing length of the dress meant we only got a peek at them.

The Mother's Day actress always finds a way to impress us with her unique, feminine, and stylish fashion choices, like this nude, asymmetrical gown, designed by the talented Donna Karan. The favorite Friends star even decided to add a touch of eccentricity to the look by wearing it off-the-shoulder. To complement her shiny attire, Jennifer opted for gold bracelets, and nude heels as well, creating one hell of a fashionable red carpet look.

Chanel Is Never A Bad Idea And Jen Perfectly Knows It

Whatever red carpet event she attends, Jennifer often receives recognition for the outfits she chooses. None more so than the Chanel Haute Couture dress she wore for the Emmy Awards in 2004.

Back then, Jennifer, 49, was nominated for best actress in the TV series that would later make her a household name. She described the dress as “Bohemian with a little bling-bling.”

Strapless, with clean lines, she coupled the outfit with fashionable sandals. Strangely enough for her fans today, Jen might not have realized that the crowning glory of her look would later become her trademark hairstyle. Quite often, she can be spotted wearing gowns that are simple, yet, so stylish and elegant. All these clean lines of her dresses are merely perfect for her tiny frame. Jen, 49, has always had a pretty distinctive sense of style and tastes when it comes to high-end fashion. In fact, the charming actress seems to be a great connoisseur of the fashion titan, Chanel, and her recent outing with Courtney Cox absolutely proves her love of the brand. The 49-year-old actress has recently stepped out in a head-to-toe black ensemble by Chanel, and it was a gorgeous sight to see as well.

Jennifer Is Seriously Infatuated With Balenciaga

If there is one particular outfit that Jennifer is best known for, it has to be this little black dress. It has reached iconic status for many women, and Jennifer knows just how to make a statement wearing one. There are countless red carpet events, movie premieres, and other celebrity occasions where she can be seen wearing her favorite little number. Yes, they come in all shapes and sizes, but the color is always the same. She wears them with very few accessories, and her footwear can be either casual or high heels. In 2009, she wore a black number designed by Balenciaga that showed off the grace of her legs. Valentino, Prada, Chanel, Armani and Yves Saint Laurent, are just a few more designers who have found a place in her LBD wardrobe. However, the one that made the biggest splash was this marvelous dress by Balenciaga that made her look super fresh, elegant and young.

There's no doubt that Jennifer, 49, epitomizes the laid-back, California-girl style that's super cute, trendy, and extra easy on the eyes; not to mention that it's surprisingly simple to pull off in no time. Apparently, Jennifer Aniston's philosophy about fashion and style revolves around minimalism.

Jennifer Simply Loves Wearing Levi 501 Skinnys

Jen almost never fails to amaze us with her casual styles, stretching from cute cutoffs to boyfriend jeans. A big favorite of hers is denim, and she chooses to wear it whenever she can. Of course, the jeans she wears can be the usual store bought brands we all know and love or the designer variety. Obviously, it appears that her love of Levi 501 Skinnys also seems to be another cool and chic item in her wardrobe.

For instance, Jennifer's Levi 501 jeans are synonymous with classic denim styling, and Jennifer chose to wear a skinny fit pair when she helped to celebrate WE Day in Los Angeles. The jeans were not the traditional style we're used to seeing from Levi. Instead, they were slim-fit with a tapered leg. The full ensemble included a pair of platform sneakers, black blazer, and a printed t-shirt. What could be simpler than that? The cool thing about this outfit is that anyone can give it a go. She has also managed to add her twist to wearing jeans and often cuffs them at the ankles. This means her cute ankles can be appreciated as well as the footwear she has chosen. Following an injury, she was forced to wear a wrist brace. However, in true Jennifer style, she wore one that matched her outfit and looked like it was meant to be part of her lovely ensemble.

That Ripped And Distressed Style Is Just Too Cute To Handle!

Who says you have to dress up to go out for dinner with your beau? Jennifer doesn't think you need to, so she often puts on her favorite pair of jeans for a dinner date. She has been spotted wearing ripped skinny jeans by GRLFRND, as well as boyfriend jeans from Levi's. It seems like it might be one of her favorite brands. In 2017, she was following the trend for ripped and distressed, and she most certainly looked good and super casual in them. The jeans she wears are sometimes paired with sneakers but look equally good, and far more glamorous when coupled with strappy sandals.

There's something about wearing jeans that makes Jennifer look very much like the girl next door, rather than a Hollywood movie star. She carries the look off very well, and it's a style we can all aspire to.

With such items in your wardrobe, you can easily copy her natural look. Apparently, this lady's not only a phenomenal actress but a hopeless shopaholic at heart! Jennifer, 49, paired her ripped jeans by GRLFRND with Stuart Weitzman sandals, which were like the icing on the cake.

For a leisurely stroll around NYC, Jennifer donned a casual, yet chic, outfit while flaunting her killer physique in a white tank. Jen looked as pretty as always, and the world can't help but wonder how much Justin regrets letting her go.

Jennifer And Her Beautiful Affair With The Strappy Heels

Jennifer loves her strappy sandals, and it doesn't matter what else she might be wearing. It could be an elegant, little black dress or casual denim jeans. So, she also wore a black multi-strap pair designed by Gianvito Rossi when she attended the premiere of The Leftovers, Season 3.

For this occasion, she had chosen a leather short black dress that revealed one bronzed shoulder and showed off her gloriously tanned legs.

Aquazzura is another footwear designer she likes to wear, along with the famous, Jimmy Choo. She has been quoted as saying “The higher the heel, the closer to heaven,” and she seems to follow this philosophy on many occasions. Even though she can often be found wearing far more casual footwear, she's not shy in dragging out the heels. Strappy sandals and wedges seem to be particular favorites. Color doesn't seem to matter here; it can be a striking red or black, but it needs to compliment her outfits.

Although she doesn't follow the trends blindly, Jen has always looked simply perfect. The actress, who's now in her early 50's, believes that everyone has the right to choose what's beautiful and what's not; and this applies to the fashion industry as well. Jen almost resents the whole fashion thing and there's a reason for it. She believes that the celebs, in particular, are always scrutinized when they wear the same thing twice.

"I almost resent the whole fashion thing...and that rule about never wearing the same thing twice. We get to decide for ourselves what is beautiful when it comes to our bodies. That decision is ours and ours alone," the actress said in an Op-Ed for The Huffington Post.

Jen's Sporty Looks Are The Ultimate Fashion Inspiration

She might be okay with wearing glamorous strappy sandals, but Jennifer is also the queen of casual footwear, too. She's not afraid to wear comfy sneakers, flip-flops, or canvas shoes when walking around town. Besides, everything she wears looks great on her, and her beauty simply shines from within. Maybe it has something to do with her healthy glow, and perhaps it's what makes her outfits look ultra chic and modern. She is also able to mix and match different styles as well.

For instance, matching sneakers with elegant dresses or strappy sandals with ripped jeans is a piece of cake to her. Everything she wears seems to go together entirely, and there is little need for fancy accessories. Her makeup is always more natural looking and the hairstyle she has been sporting for years matches everything she wears. If she feels the need for jewelry, it will be simple and elegant. Bags are also super simple and appear to be functional, making a stylish statement, but very quietly. Unlike many other celebs, who simply cannot live without their fancy entourage, Jen doesn't shy away from such casual but super chic looks, and that's perfectly fine. Besides, the actress looks just as pretty and feminine with or without her makeup artists and stylists, and this particular look proves it.

Jennifer's Hairstyle Is Favored By Lots Of Ladies

Jennifer's hairstyles have changed very little over the years and have always been more of a variety of similar looks. In fact, you can go to your local salon and ask for “The Rachel.” Even though there were no more Friends episodes made after 2004, her signature hairstyle lives on. She has tried many variations over the years, including a wavy style and sun-kissed brown color in the first season of Friends.

She also worked the color black for a while in 1992, before returning to the color she is most famous for— blonde.

Her favorite way of wearing her hair is natural, but on occasions, she has been known to wear it up. One look that possibly wasn't her choice and not one many of her fans will want to emulate, was the fake dreadlocks she wore for the 51st Emmy Awards. She may have tried a few different variations over the years but always returns to the one she is so well-known for. The layered, natural, shoulder-length look is just the perfect one for her, and we totally approve of it.

Jennifer's Pictures Of Doing Yoga Will Improve Your Day

For many women, Jennifer has a look to aspire to. She always manages to look cool, and her style is effortless on the eyes. When it comes to her makeup, there is little required to show off her California beach babe look.

Nude and understated colors mean she never looks done up, only naturally beautiful. She's never said that her trim figure and healthy looking skin don't come naturally.

On the contrary, she spends at the very least 20 minutes running or spinning every day; and that's quite an important cardio session that ensures she stays trim. Apart from this, she's also a devotee of yoga, which also improved her posture. She is a confident woman who knows her best features and is not afraid to show them off. Many of the outfits she wears exposed parts of her toned body for everyone to see. Her hairstyles aid in her natural look and she often prefers to wear it down, even for the most prestigious of occasions.

Jennifer may have started off her Hollywood red carpet appearances in jeans, way back in 1998, but she has developed her unique style and can easily carry off elegant gowns and unusual eye-popping creations. Her beauty is natural, and this shines through whatever she is wearing or doing.

That's One Hell Of A Street Style (That Deserves An Award Too)

Looking pretty, stylish, and casual at the same may sound like an oxymoron, but it's an easy job for a gal like Jennifer. This lady knows how to pull off any look without even stressing about it. Over the years, we've noticed that Aniston's everyday style is super casual and sweet, although, it cannot beat her typically sophisticated red carpet looks. However, it hardly means that her love of ripped jeans, classic sneakers, and plain t-shirts aren't hot as heck.

From her chic pairs of denim cutoffs and boyfriend jeans to her fancy skintight dresses, Jennifer's sense of style will undoubtedly make your head spin.

In the above picture, we see Jen's deceptively simple, yet super trendy and stylish, approaches to fashion. Evidently, she, too, believes that beauty comes from within, and we can't agree more with it.

"[Beauty is] inner confidence. Peace. Kindness. Honesty. A life well-lived. Taking on challenges and not feeling shame for things that haven't gone the way you felt they should have," the actress told People in April 2016. "And not feeling like a failure or allowing people to critique your life and make you feel like you've failed at something. That's just toxic noise."

This Black Jumpsuit With A Plunging Neckline Is A Real Masterpiece!

The charming Friends actress, once again, wowed the world when she stepped out in this amazingly hot, black cropped jumpsuit. As a natural consequence, she inevitably made the headlines around the world. Realistically, it can't be otherwise, especially with Jen's refined sense of style. The charming actress, who's recently parted ways with her longtime love, Justin Theroux, added a splash of color to her look by rocking a pair of cherry-red high heels. Frankly, Jen's certainly created one hell of a provocative look that accentuates her mature beauty and femininity.

The actress, who rarely rocks bold accessories during the day, has been spotted around NYC wearing some statement pieces. She may be single now, but it doesn't mean that she needs to hang her head in sorrow because things fizzled with him.

While Jen has been quiet about it, Justin has already opened up to the tabloids, and specifically to Mastermind Magazine. “I just keep working, which is the only thing you can do,” he said. “So, when someone I’ve never met in my life comes up to me and asks me a personal question, I say ‘I don’t know what you’re talking about.’ And you know, I’m sorry, but I really don’t.”

Jen's Floral Dior Dress Is Ideal For The Summer Season

Well, Jennifer's typical boyfriend jeans and tank tops may look really cute on her, but nothing can beat the elegance of her Valentino, Dior, or Alexander McQueen attire. Not only does she look incredibly charming and stylish in them, but Jen just proves that less is always more. While her Levi jeans and cutoffs are her daily uniform, it's also fun to see her rock such floral dresses, like this gorgeous Dior dress. The cherished actress embraced her girlie side when she paired this pretty dress with suede Casadei heels. Although it's been about 20 years since stepping into the spotlight, Jennifer still finds it easy to rock that girl-next-door look.

This floral dress is another great look she can pull off easily and quickly. Apparently, that's her go-to for the summer reason and she looks pretty awesome like this.

Arriving at the premiere of We're The Millers in London, Aniston turned heads in her flirty cotton and silk dress, which made her look super cute, young and fresh. Hopefully, Jen will continue trying out new styles, especially when promoting or attending big movie premieres, like this one.

Jen Didn't Make A Mistake When She Opted For An Alexander McQueen Dress

There's no doubt that Jennifer's red carpet style has seen many stages of transformations. However, if you ask her, she'll probably say that the secret to her beauty and perfect style comes from within. To her, it's all about self-expression and confidence in oneself. Frankly, Jen's minimalistic approaches to fashion actually prove the point.

She may be working with top stylists, but she hardly ever abandons her signature style. Besides, Jennifer has been known for her love of yoga and cardio, sculpting her body so well.

Here, Aniston shows off the incredible results in a waist-cinching ensemble designed by the fashion beast, Alexander McQueen. For the premiere of her ex-husband's TV series, Jennifer Aniston donned a leather LBD, which featured cap sleeves and a cute pleated skirt. To finish it all off, Jennifer added some texture to her stylish ensemble with a crocodile Givenchy clutch and a McQueen leather corset belt. Moving on to her fancy footwear at the premiere, Jennifer opted for an elegant pair of suede platform pumps, designed by one of her favorite brands, McQueen.

Looking Fabulous Outside Grauman's Chinese Theatre In Hollywood

Jennifer Aniston made all women green with envy when she arrived at the Grauman's Chinese Theater in Hollywood in this gorgeous dress. Jen paired up her lovely Prada dress with fancy Gucci shoes in a nude color, creating some mega-chic daytime wear. Dipping her hands, fingers, and toes into this wet cement may sound like a terrible fashion idea, especially given her fancy outfit, but Jen was careful to keep her shiny accessories away from it. Among the attendees were Chelsea Handler, Jason Bateman, and her ex, Justin Theroux, who didn't miss the special day either. Later on, Aniston sat down for a quick chat with Chelsea Handler, where she opened up about her recent split from Justin, latest projects, and her future plans as well. At some point, Jen even hinted that the filming The Break-Up was like a getaway from the reality; it really helped her "turn the page and move on."

Now that she's single, we can't imagine how many guys are just waiting for the right time to ask her out; and it probably makes Justin Theroux feel terrible because of it.

Jen Looks Hot In Her Roberto Cavalli Dress

This boho-styled dress from Roberto Cavalli's spring collection is, hands down, one of Jen's best looks so far. The actress, who's been letting loose in her wardrobe picks lately, finally decided to try out an excitingly new style. From her classic red gowns to her chic jumpsuits, Jen has apparently established a thing for more feminine and stylish outfits.

This time, Jen dared to put on this eye-popping dress designed by Roberto Cavalli, and it made her the star of the night.

Arriving at the Office Christmas Party LA premiere, Jennifer stunned in her multicolored embroidery with shimmery beads all over. The beautiful Cake actress looked great in her Roberto Cavalli dress, while its semi-sheer fabric accentuated her enviable figure in all the right places. Despite the easy-breezy style of the dress that many wouldn't wear at a red carpet event, it was just an ideal fashion choice for the night. Jen's bohemian frock featured a lovely feathery detail at the side of the skirt, giving a final twist to Jen's overall styling here.

Jen Glows In Her Saint Laurent Dress (And Justin Probably Hates Himself For Losing Her)

Apparently, beaded gowns seemed to be a favorite for Jennifer in 2015, as she also chose one for the Golden Globes. This time, the color was black and the dress was a custom Saint Laurent. Once again, she decided to wear her favorite black dress for this glamorous event— and what a black dress it was! It featured a halterneck and sequined top. A cummerbund accentuated her gorgeous figure, and the thigh-high slit in the dress showed off her beautifully tanned legs. A different hairstyle was the order of the day this time as she went for a glamorous updo, and, once again, very few accessories were necessary. She wore her hair slightly differently for this occasion in that it was worn up rather than her usual shoulder-length layered look.

For the special night, she chose to add strappy sandals and onyx earrings. Her grande appearance at the Golden Globes was eventually considered to be one of her best red carpets looks ever.

Arriving at the event, Jennifer Aniston just wowed the audience with her spectacular Saint Laurent gown. The charismatic actress, who was honored with a nomination for her smooth performance in Cake, might have opted for her signature makeup look again, but she definitely rocked a rather new hairstyle. At 49, Jennifer looks younger and happier than ever, despite her recent split from her ex-husband, Justin Theroux.

References: popsugar.co.uk, eonline.com, fashionmagazine.com, telegraph.com, instyle.com, denimology.com, stylebistro.com, goodhousekeeping.com, glamour.com, elle.com