Times Jennifer Aniston Should Have Landed On The Worst-Dressed List

Jennifer Aniston is renowned for her flawless, timeless style. Still, even she manages to occasionally put a fashionable foot wrong, making for a frock faux-pas worthy of topping all the worst-dressed stars lists in the biz. However, even worse than worst-dressed, perhaps, is most boring.

The stunning transformation of Aniston from a teen to an A-lister is pretty remarkable. She went from high school drama geek to Hollywood it-girl in the blink of an eye. But sometimes, it feels like all of Aniston's looks are the same: classic black tailored couture. Her seeming reluctance to step away from the tried and tested monochrome red carpet standard leaves many a fashionista yawning. A 2010 Glamour poll asked readers if they were over Aniston's predictable style. 51% begged her to "put on red lipstick, try a long bob, go brunette — SOMETHING, after all these years."

It's unlikely Aniston will undergo any major makeover any time soon, though — and let's face it — if it's not broken, don't fix it. Especially given the fact that when she has mixed it up a bit and stepped out of her style comfort zone, it often resulted in major fashion fails. We're looking at some of the times Aniston's clothing catastrophes should have landed her on the worst-dressed list.

Jennifer Aniston threw caution to the wind and stepped out of her usual classic and safe style when she attended the 5th Annual Screen Actors Guild Awards in March 1999 with her "Friends" costars Courteney Cox, Lisa Kudrow, Matt LeBlanc, Matthew Perry, and David Schwimmer. Aniston plumped for a black sateen-look, belly-baring, strapless scarf top and pelvis-exposing matching maxi skirt. Sadly, despite undoubtedly costing a fortune, the outfit looked like it'd been grabbed off the sale rail at Forever 21 or cobbled together last minute by her nan.

Still, Aniston was perfectly tanned and toned, working it for the camera. Being a red carpet veteran, it's little surprise that she always knows how to put her best foot forward, especially given that her stylists, twin sisters Nina and Clare Hallworth, regularly coach Aniston on how to nail the perfect Blue Steel.

"They go, 'Never do this! Always do this!' I'm like, 'Well, that feels weird.' I don't know how to stand on a red carpet, but you do the best you can," Aniston told InStyle in September 2021. "I also try to connect with those people holding cameras. Some of them I've known for a long time, so I'll say hello. If I'm having an honest interaction with someone, it makes it easier."

Jennifer Aniston suffered a major fashion fail in September 1999 when she walked the 51st annual Primetime Emmy Awards red carpet with Brad Pitt. While he was dressed in a monochromic gray suit and shirt with a blond 'do that screamed "Business up front and party in the back!" she plumped for a more glitzy and ... well, interesting ... look.

Aniston's usually glossy locks were a backcombed, frizzy, beachy-look mess and twisted at the top to mimic dreadlocks. She was clad in a Randolph Duke dress with paisley-shaped sequined patches sewn onto a see-through net top and what resembled an old brown curtain from the waist down. Oh, and a little gold fabric purse that looked like a Claire's original. Still, when you have Pitt as an accessory, why bother?

The awards show was the golden couple's red carpet debut, and they were firmly in the throes of love — at the mid-point between meeting and divorcing. They walked down the aisle in a July 2000 fairytale star-studded spectacular that cost a cool $1 million and featured a wall of caviar; 50,000 roses, wisteria, tulips, and lotus flowers; entertainment courtesy Melissa Etheridge, a Greek bouzouki band, and a 40-person-strong gospel choir; lobster; champers; and an over-the-top fireworks display.

Jennifer Aniston's stylists must have been on vacation when the actor attended the August 2013 "We're the Millers" premiere in London, England. Otherwise, there really is no explanation for the horrendous outfit she was wearing.

Aniston plumped for a floral horror by Christian Dior — a definite change from the simple and classic black Valentino she usually favors. As if the skater dress' saccharine sweet print wasn't awful enough on its own, there was also a white underskirt peeking out of the bottom with little pink flowers plastered all over it that looked like they were ripped straight off your grandma's best china. Oh dear.

Aniston's cutesy, kitschy look was made all the more surprising by the fact she was engaged to Justin Theroux at the time. After hooking up with her "Wanderlust" co-star in May 2011, she began dressing more in sync with his edgy, self-described "goth-adjacent" style, rocking black leather on the red carpet and combat boots on the street. "I mean, there's a really good case to be made that I haven't changed what I've been wearing since I was 14," Theroux told People in September 2024. "I was sort of emo, punk, whatever you want to call it back in the day." The writing was on the fashion wall long before the couple walked down the aisle.

Jennifer Aniston's February 2004 "Along Came Polly" Paris premiere dress proved that just because you can doesn't mean you should. As usual, she was perfectly tan and toned, but her decision to bare (nearly) all looked reminiscent of an adult actor rather than a mainstream one. Aniston was clad in a sparkly silver dress with a see-through net top slashed to the waist. She saved her modesty with some strategically placed flesh-colored cups and finished the look with a black flasher mac.

Aniston was all smiles on the red carpet, but sadly, 2004 turned out to be a devastating year for her. Brad Pitt started filming "Mr. & Mrs. Smith" in January. It's the movie where he met and fell in love with Angelina Jolie, leading to the end of his marriage to Aniston.

Jolie talked about falling in love with Pitt onset in a January 2007 interview with Vogue. Aniston responded to her comments in her own interview with the fashion bible in December 2008. "There was stuff printed there that was definitely from a time when I was unaware that it was happening," she admitted. "I felt those details were a little inappropriate to discuss. That stuff about how she couldn't wait to get to work every day? That was really uncool."

Jennifer Aniston's choice of little black dress in May 2013 most definitely should have landed her on the worst-dressed list. The actor was hosting a party celebrating the release of her yoga instructor Mandy Ingber's book "Yogalosophy: 28 Days to the Ultimate Mind-Body Makeover" at the Soho House in West Hollywood, Los Angeles, and her body was living testament to Inger's training prowess. However, Aniston's outfit was a 100% fashion fail that resulted in the tabloids resurrecting the tired old trope that haunted her throughout her thirties and forties.

Photos of Aniston's billowing waist peplum had editors salivating, sparking "Baby Bump!" front pages galore. "Jen: Pregnant Bride! Miracle baby after two years of fertility treatments. Wedding just weeks away! 'Justin loves my mommy curves!'" a Star magazine cover screamed. "Jen's big secret PREGNANT! After years of trying, she's finally going to be a mom at 44. How she's prepping for a baby — and a wedding!" US Weekly echoed.

After decades of staying schtum, Aniston finally addressed the endless pregnancy rumors in a heartbreaking December 2022 interview with Allure. "I was trying to get pregnant," she revealed. "It was a challenging road for me, the baby-making road," Aniston added. "All the years and years of speculation ... It was really hard. I was going through IVF, drinking Chinese teas, you name it." She concluded, "The ship has sailed."