Outdated Trends Jennifer Aniston Has Been Caught Wearing

Just like the rest of us, Jennifer Aniston has occasionally sported an outdated getup or two. The stunning A-lister occasionally catches us by surprise by walking out in skinny jeans, aviator sunglasses, and dated pantsuits. While Aniston is undoubtedly beautiful enough to pull off anything, the out-of-date pieces can be a little unusual for someone so good at setting trends. 

What's so funny is that Aniston is the embodiment of the best of '90s style, so it's entertaining to talk about her in terms of fashion trends. No one could pull off Mom-jeans like the "Friends" star, or rock a crop top with quite the same panache. And since we're all in a nostalgic wave for the bygone era of the '90s, we often look back at everything Aniston has loved to wear and look to her for inspiration on how to rock strappy dresses, floor-length column dresses, and chunky soles. However, as we all know, some dated trends are back in style, but others are decidedly not. What we're narrowing in on are Aniston's more recent looks that didn't hark back to the beloved '90s, but rather the early aughts or the 2010s. And these decades are serving less nostalgia, and more outdated cringe. 

For the premiere of her Netflix film "Murder Mystery," Jennifer Aniston walked the red carpet in June 2019 wearing a leather mini dress. The Celine dress featured a mock neck, and cinched at the middle with a belt. What made the dress so difficult was its boxy shape, awkward, bulky pockets, and ruched leather along the torso. Aniston paired the Celine piece with studded, gladiator-style heeled sandals, which were a bit of a mismatch. While she always looks good, there was so much about this particular look that felt dated. The boxy cut of the leather dress invoked the biker-chic style of the early 2000s, as did the bejeweled, gladiator sandals. The busy, heeled shoes certainly fall under accessories that are totally outdated in 2024, but Aniston's best accessory of the night was movie buddy Adam Sandler; friendship never goes out of style! And we have to give her hair points. Her shoulder-length blowout with vivid highlights was a flattering and youthful hairstyle. Thankfully, that saved the look. 

In 2019, Jennifer Anniston arrived at "Jimmy Kimmel Live" wearing her signature all-black look. Aniston has perfected this sleek, monochromatic style over the years, and we love to see her strut her stuff. The only problem with this particular choice is that "The Break-up" star styled the look with black skinny jeans. This has been an ongoing debate between generations — Gen Z has declared the death of skinny jeans, while Millennials and older generations are still holding out hope that the denim cut will come back around. Of course, most of us have accepted the end of skinny jeans, and learned ways to style loose denim, because that look is more fresh and modern. However, Aniston went full-on 2009 with this look, by tucking her skinny jeans into ankle-length, heeled booties. Her gorgeous hair and structured blazer saved the day, but the outfit would have passed the test had she gone for a wider denim cut.

In October 2019, Jennifer Aniston arrived at "Good Morning America" in New York City sporting some very unique eyewear. She appeared on the early morning talk show alongside Reese Witherspoon to share about their new series "The Morning Show." Aniston wore a white, collared mini dress with a long black coat, gold hoop earrings, and simple, heeled sandals. The outfit looked great. The only hiccup was Aniston's choice of orange-tinted aviator sunglasses. Vogue called it the return of the "sleazy sunglasses," but aviators never took off after that, even with Aniston's power of sartorial influence. Aviators were hugely popular in the early 2000s when big-framed shades of all sizes were trending hard. Sunglass styles have evolved over the last twenty years, getting smaller and sleeker. Modern cat eye sunglasses and small shades, evocative of the '90s, are back in business, but the aviators never returned to the mix, and certainly not orange-tinted aviators. Sorry, Jen. 

It's tough criticizing a diamond necklace, but we're going to anyway. In 2020, Jennifer Aniston wore her signature all-black look to the Golden Globes, where she was nominated for her series "The Morning Show." She wore a black, Dior gown featuring a trumpet-style neckline, and wore a double-stranded diamond necklace by Fred Leighton. While diamonds are diamonds, the large statement necklace served 2010 vibes, back when we were all rocking faux diamonds and pearls. Of course, in Aniston's case, the diamonds are real, which does lend some legitimacy. Nonetheless, the double strand and oversized statement style of the jewelry harked back to a bygone era. Aniston did something similar for the 2020 Emmys. She wore a black gown and rocked a triple-strand diamond necklace. While it's obvious that Aniston loves her diamond necklaces, we can't get over these particular style choices. But since most trends come around again, Aniston might be in luck, and hopefully, statement necklaces will be chic again soon. 

At the Critics Choice Awards in 2024, Jennifer Aniston swapped her traditional gown for a black pantsuit. The choice was unexpected when looking back at the stellar arc of Aniston's red carpet choices. The Dolce & Gabbana jumpsuit featured feathers on the bodice, tapered slacks, and a long, satin sash. Once again, Aniston was nominated for her role in "The Morning Show," and while her TV performance has been consistently stellar over the decades, the choice of a pantsuit and sash was a bit of a setback. Around 2015, we saw a craze of celebrities wearing jumpsuits on the red carpet that were sprouting all kinds of abnormal fabrics. Diane Kruger rocked a red jumpsuit that couldn't decide if it was more slacks or a cape. Chanel Iman did something similar in 2016, when she wore a white, strapless pantsuit that featured the back of a skirt, as well. Aniston — as well as these other women — looked lovely in their pantsuits; the problem was the addition of unnecessary fabric that made the outfit seem older than it was.