The Most Outdated Outfits Jennifer Aniston Has Ever Worn

Jennifer Aniston kicked her career off in the late '80s, and ever since then, she's been a staple in the entertainment industry — whether we're talking about hit shows that we can't binge enough of or Hollywood blockbusters that have us at the edge of our seats. Over the years, Aniston has also claimed the title of a true fashion and beauty icon, as her transformation was always astounding, showing fans across the globe that one can radiate power and beauty in their 50s just as enthusiastically as they did in their 20s.

Of course, being in the spotlight isn't all sunshine and rainbows, and stars like Aniston, who have been successful for so long, certainly know that. So, while we adore the actor for her talent and undeniable charisma, we have also noticed that she tends to hop on fashion trends that aren't as hip anymore. From outfits that just didn't age well to pieces that actually weren't even trendy when she was seen in them — here are Aniston's most outdated looks!

In June 2017, Jennifer Aniston was spotted at LAX in an outfit that was pretty popular at the time—but we can't imagine seeing celebs wear it today. We're talking about ripped and cuffed skinny jeans. As with most very specific trends, they eventually went out of fashion, replaced by baggier silhouettes.

Of course, ripped jeans have been popular since their breakthrough in the '70s, and there's no doubt that some form of the rebellious statement piece is always in style. However, instead of having them in the form of skinny jeans and pairing them with high heels and a button-up, nowadays, it's more trendy to have them in the form of long baggy jeans and pairing them with a casual top and a pair of fun sneakers. Trends have changed, and this Jennifer Aniston 'fit simply didn't age well.

Y2K fashion had its major revival in the early 2020s, with numerous millennial trends for the era coming back. In January 2024, Jennifer Aniston attended the AFI Awards luncheon in a very early aughts-coded outfit. However, the nod to Y2K fashion is, at this point, already a bit outdated — and with that, her choice of attire isn't really that fashionable anymore.

The actor rocked a slim, patterned maxi skirt with a black crisscross halter top — both of which were essential wardrobe pieces in the 2000s. Unfortunately, the addition of the blazer made the outfit less stylish, resulting in a look that gives 'aunt stuck in 2003' vibes rather than a cool Hollywood star. Jenn may have tried to hop on the Gen Z Y2K trend, but unfortunately, her interpretation fell flat as it was a tad too literal and a bit too late.

When it comes to big industry events, Jennifer Aniston is usually a pro at dressing up. However, for the Golden Globe Awards in January 2020, the star disappointed us a bit. Aniston opted for a classic black gown — however, its exaggerated neckline was giving us a late 2000 vibes. Not to mention that the Dior Haute Couture gown was a safe and expected choice, all things that red carpet fashion shouldn't really be about.

Necklines like the one Aniston wore in 2020 were popular in the late 2000s when stars like Nicole Kidman and Natalie Portman pioneered the trend. Even though Aniston may have thought that she could bring this type of neckline back, it's safe to say that she failed and we really do hope that necklines like this one — which just looks messy — will remain a trend of the past forever.

While Y2K fashion had its good moments, dresses over pants definitely weren't one of them. And while we can't really blame Jennifer Aniston for hopping on the trend back in May 2002 for the 75th NBC Anniversary Gala, we also can't help but cringe at her outfit today.

Yes, her wrap dress situation was sheer, and wearing it on its own would have been too much — but unfortunately, that doesn't justify the entire look. In fact, she could have easily worn it over a simple black slip dress, and this would have been a beautiful outfit. Instead, she wore it over black pleated pants, and here we are 12 years later, getting our blood pressure raised by a fashion trend that is hard to believe people thought of as cool at the time. And before you come at us, we have lived through the era (and may or may not have even succumbed to this particular trend), so we're allowed to be a bit judgmental.

In the '90s and 2000s, statement belts were all the rage, and while we can get behind them when they actually served a purpose, it's hard not to notice how silly they look with clothes that don't need them. In July 1990, 21-year-old Jennifer Aniston attended an NBC pool party, and for the event, she wore a black tank top and a funky patterned maxi skirt.

The addition of the chunky belt was undoubtedly a trendy choice at the time, but today, it would certainly be considered unnecessary. Of course, young Aniston was still exploring fashion and finding her style at the time, which is why we can't really blame her for rocking an accessory like this. Unfortunately for her, this is still an outfit that is outdated today.

We might get under fire for saying this, but the sneakers and blazer combo has been seen so many times that it just became overdone and unimaginative at this point. And fashion is so much more than looking like everybody else.

In April 2018, Jennifer Aniston attended the WE Day California event, and for it, she opted to wear a pair of skinny cuffed jeans, white sneakers, a white tee, and a black blazer, aka every girl's daily uniform at the time. While any blazer and sneakers combo is a bit outdated, it is, in particular, the black blazer and white sneaker outfit that was so overly worn at the time that it became one of those fashion staples that just isn't fashionable anymore. However, this trend was very easygoing and simple, which is why we wouldn't be surprised to see it cycle back in the future. But for now, this Jenn Aniston look remains outdated.

It seems as if the Golden Globes are an industry event that Jennifer Aniston doesn't dress her best for, as this is the second look from the event that is outdated. In January 2024, she showed up at the annual event in a black Dolce & Gabbana gown, but unfortunately, the choice wouldn't put her on a best-dressed list.

While the dress isn't horrible, its design is a tad outdated and not in a retro-cool way. In particular, the skirt part of the dress, which was covered in a scallop (almost mermaid-like) design, is something we've seen plenty of over the past two decades. Numerous stars (like Miley Cyrus at the 2009 Academy Awards and Charlize Theron at the 2016 Cannes Film Festival) have rocked scallop dresses, making it an overdone trend and Aniston's 2024 gown design outdated.

The 2010s had lots of trends that seem odd today, and one of them was undoubtedly the chunky scarf. Of course, a warm and cozy scarf will always be stylish when the weather is cold, but in the 2010s, the outside temperature was irrelevant when rocking this trend. And this brings us to Jennifer Aniston in 2011.

The star was spotted in New York City that November in an outfit that not only didn't age well but also made no sense. The chunky purple scarf wrapped tightly around her neck indicated that the weather must have been freezing, but Aniston didn't wear a jacket. Instead, the actor was wearing a white top and black blazer — both of which surely couldn't provide enough warmth. While the 'fit may have been considered stylish at the time, we'd like to think that today's trends are a bit more logical than this one.

When it comes to fedora hats, some love them, and some hate them — and while we belong to neither camp, we can't deny that they are an outdated trend. The specific hat was very popular in the 2000s when celebrities like Paris Hilton and Christina Aguilera even rocked it on red carpets, and it was equally often seen on men and women.

Jennifer Aniston was a fan of this trend, and the actor was frequently seen wearing one when out and about. In fact, Aniston didn't give up the fedora for a while, and she was even seen wearing it in the mid-2010s. Of course, a hat like this could provide some additional privacy as the star was less recognizable, but that doesn't change the fact that it looks a bit ridiculous nowadays — especially when also paired with sunglasses and a chunky scarf. Luckily, nowadays, there are more stylish ways of hiding a bad and greasy hair day!

While some are fond of the blazer and flip-flops combo, if you ask us, the trend should be outlawed. Okay, maybe we shouldn't go that far — after all, fashion should always be a form of self-expression — but we can't help but feel nauseous just at the thought of combining the two pieces.

Jennifer Aniston was spotted wearing a pair of black flip-flops with a classic black blazer in May 2013 and we're certainly hoping that this look will remain outdated forever. The Hollywood actor is the type of star who can pull off a lot of different fashion styles, and she looks beautiful even in this outfit — but the combination of beachwear and businesswear is just something we can't get behind.

The so-called cold shoulder trend has been around since the 1930s, and while it's a style that many may consider timeless, we'd like to argue that it depends on the execution. In the 2010s, a specific, edgier form of shoulder cut-outs became popular, and Jennifer Aniston was one of the first celebs to embrace it.

For a 2010 premiere of her blockbuster "The Bounty Hunter," Aniston wore a cream-colored cold shoulder dress with an additional cut-out on one shoulder. The asymmetry and placement of the cut-out make it very 2010s, and nowadays, a dress like this just wouldn't pass as fashionable. Of course, just because a look is outdated doesn't always have to mean that it isn't stunning — unless we're talking about the blazer and flip-flops combo, of course.

Anyone who lived through the Y2K era of low waistlines will tell you that the trend was not only unflattering but also incredibly uncomfortable — especially when bending over or sitting down. However, we're willing to embrace it again as Gen Z is all about showing off their hip bones, but we draw the line at tiny low-waist denim shorts with pockets that are visible below their hemline.

It was exactly those kinds of shorts that Jennifer Aniston was seen in back in July 2013, and while they were trendy at the time — and Aniston's legs look stunning in any kind of shorts — we truly hope this type of bottom doesn't return for future summers. Don't get us wrong — we have nothing against short shorts; after all, if you have it why not flaunt it — but the infamous deep pockets just seem unnecessary, and we will die on that hill.

Toward the end of the 2010s, leather leggings had their major moment, and while their style was chic and edgy for colder months, anyone who has a pair in their closet knows that, unlike regular leggings, leather ones are rather uncomfortable. While trends come and go for various reasons, we believe that part of why leather leggings left the fashion chat is because they aren't easy to clean, and you also tend to sweat quite a bit in them — especially if you're rocking them on a night out.

Jennifer Aniston was a fashionable girlie who jumped on the trend in the late 2010s, and she totally pulled it off. However, even though her 'fit from December 2018 was an example of A+ fashion at the time, were she to rock the same pieces today, her look would be very outdated.

The skinny jeans and flowy cardigan combo had us all in a chokehold in the 2010s, and Jennifer Aniston rocked the trend like a pro. In July 2016, Aniston was spotted in Los Angeles in a chic black and off-white flowy cardigan that was the epitome of trendy fashion then.

Fast-forward eight years, and this fit is rather outdated. With the switch from skinny jeans to baggier denim, a shift in accompanying cardigans became noticeable, too. Instead of long and flowy, the trend shifted toward classic cardigans that were either cropped or hip-length. And just like that, a cozy 2010s staple that plenty of us thought of as a timeless piece became out of style.

When it comes to wrinkled fabric, some love it, others hate it — and no matter how trendy it may be, their minds won't change. As you've guessed, we fall into the latter as we can't understand the appeal of a clothing piece that is wrinkly. Of course, there are exceptions and celebs who look incredible in literally anything, but most of the time, a piece of clothing made from a wrinkled fabric just looks underwhelming. And more often than not, the fabric ends up distracting from the silhouette.

Jennifer Aniston wore a wrinkled bustier mini-dress to the Women In Film 2009 Crystal And Lucy Awards, and while we can't claim that it didn't look great in person — it certainly didn't photograph well. The material, which seemed to be satin-like, was wrinkled unevenly, and while Jenn still looked beautiful, her dress just didn't do her justice.

Satin and silk are materials that never go out of style, but the clothes made from them certainly do. When Jennifer Aniston attended the Los Angeles premiere of the 2009 movie "He's Just Not That Into You," she walked the red carpet in black satin pants and a matching blazer.

At first, that may not seem outdated, but today's satin/silk pantsuit trends are noticeably different from those of the 2000s and 2010s. Jenn's 2009 pants are rather tight around the top, which means that underwear lines are inevitable — and the short blazer isn't helping either. Unlike then, nowadays, satin sets consist of looser-fitting pants and a matching oversized blazer, creating a silhouette that is a lot more forgiving and a set that is super comfortable. While Aniston's 2009 look isn't awful by any means, it is definitely giving us fashion that we can specifically place in that era without even researching the year — which is hard with Aniston, who hasn't visibly aged a day since the early aughts.