Jennifer Aniston, on-screen darling since she became Rachel on Friends, has the kind of career and style evolution that everyone envies. From coming to prominence as an actor in the 1990s, then absolutely skyrocketing to fame, then continuing to act in interesting TV and film projects for literally decades, she's been in our lives for a long time. And, luckily for us, she also has a cool and fun red carpet presence, usually opting for chic and simple styles (but sometimes taking big fashion risks, as you'll see). She's had some amazing moments over the course of her career, both sartorially—just wait until you see some of these gowns—and socially. Over the years, people have...really, really cared who Aniston was dating and/or married to, and Aniston has brought some of her partners to the red carpet with her. She knows how to be just communicative enough around her love life to keep us entertained but doesn't share too many details.
Keep scrolling for Aniston's incredible dresses, sneak peeks into her love life, and wonderful combinations of both.
At the NBC Stars Party, 1990
Aniston landed some TV roles in the 1990s, and played Jeannie Bueller on NBC's Ferris Bueller (based on the movie, naturally). At this NBC party, one of her very first event photos, she's casual in denim, a grey satin shirt, and casual wavy hair.
With Charlie Schlatter
Here she is with her costar Charlie Schlatter, who played the titular Ferris Bueller on the show—which only aired for a single season, FYI. (Apparently, the two briefly dated.)
At an NBC Pool Party, 1990
At this casual 1990 NBC party, Aniston wears a very '90s black tank top, chunky belt, and maxi skirt. Even though things are about to get a lot more formal for her, I truly love seeing early-days Jen rock some appropriately casual teen outfits.
At the NBC Press Party in 1995
As soon as Friends debuted in fall of 1994, the cast member became household names almost overnight. With each actor holding Central Perk-worthy coffee mugs, this is one of the first event photos taken after the series began its meteoric rise to fame.
At the 1995 People's Choice Awards
At one of their first awards ceremony, here Aniston shows off a famous early iteration of her "Rachel" haircut with stars Matthew Perry and David Schwimmer.
At the 1995 People's Choice Awards
Aniston keeps it simple, and coordinated, in a black tank dress for the event. (Friends won a People's Choice Award for Favorite New Television Comedy Series, obviously.)
At the 'Fight Club' Premiere, 1999
By the time of this 1999 premiere, gossip magazines had been buzzing: Were Aniston and Brad Pitt, arguably two of the most popular actors alive, actually dating? This was their first red carpet event and confirmed it with a resounding yes. Aniston's still working her simple, chic, aesthetic, but still fun separates with a middle slit in the shirt.
At the Emmys in 1999
We're not sure who made this particular gown, but at this point Aniston is starting to come into the red carpet style she'll be known for her entire career, here seen with Pitt, who'd by then become her husband. Somewhat more perplexing is the "relaxed beachy waves" she's doing, a beloved choice for '90s style that reads more "messy" today.
At the Warner Bros' 2000 Emmys Party
Aniston doesn't always lean into color, but when she does: It's exceptional. This simple red Prada column gown (keeping things simple with a small bag and matching red lip) makes this one of her most iconic early outfits.
At the Golden Globes, 2002
Once again utilizing her husband as the best accessory, Aniston delves into pantsuits here. She often favors a gorgeous dress, but here the blazer (worn as a top) is just the right amount of chic—plus, a twinning moment with Pitt. I'm confused about the sunglasses, but whatever!
At the 2004 Emmys
Proving that simplicity is often the key to her incredible red carpet style, Aniston's simple Chanel dress was deemed one of the best Emmy dresses of all time.
At the Golden Globes, 2004
In vintage Valentino, Aniston goes bold (and shows a rare daring moment)—but it won't be the last time she experiments with her "simple and classy" aesthetic to absolutely brilliant effect.
At the 'Troy' 2004 Cannes Premiere
In a similar way, this beaded halter top Versace gown (which she was wearing to support Pitt for his movie premiering at Cannes) isn't over-the-top in terms of color or detail, but that's the brilliant simplicity of it.
At "Going Upriver: The Long War of John Kerry" Movie Premiere in 2004
Honestly, Aniston's casual style is just as good as her haute couture red carpet fare (this simple blazer and denim would work just as well today. Less fun: In May of that year, rumors had started of Pitt and his costar Angelina Jolie possibly getting romantic. This photo was taken in October, and Aniston and Pitt would formally divorce in March 2005.
At 'The Break-Up' Screening in 2006
We have now entered the "short, sparkly, and utterly fabulous" portion of the slideshow (and frankly, she deserves it). I love this metallic slip dress, particularly how it's out of the color family she usually chooses in her red carpet couture. (While they didn't pose together, Aniston was dating costar Vince Vaughn).
At the 2009 Women In Film Crystal + Lucy Awards presented by MaxMara
Another one! This slip dress looks like it's made of hammered gold, and I forgot how amazing that color looks on her. At the event, Aniston joked about how her love life and professional lives were running in parallel: "If any of you have a project entitled 'Everlasting Love With A Stable Adult Male' I'm at table 6 and my agents are at table 12!"
At the Paris 'The Bounty Hunter' Premiere, 2010
I'm going to go on record to say that this pink Christian Lacroix dress might be one of the most fun things she's ever worn. (And yes, your memory serves you correctly: Yes, Aniston and Gerard Butler briefly dated.)
At the 2011 ELLE's 18th Annual Women in Hollywood Tribute
I love this Kaufmanfranco minidress so much. It's mini, it's plunging, it's sparkling, and it could not be fitting her better. A++.
At the Hand and Footprint Ceremony, 2011
Firstly, this printed Prada dress is fabulous and I want her to wear more of it (she reused it at least once!). Secondly, this was the first official red carpet event that Aniston appeared with husband-to-be Justin Theroux, clearly having a blast in the audience.
While Signing Bottles of "Jennifer Aniston" in 2011
If you're going to be signing bottles of the perfume that you made and has your name on it, you'd better be doing it in this gorgeous Vivienne Westwood. Aniston should always dress in this color, I firmly believe.
At the 2013 Oscars
Like I said, when Aniston does color, she does it right: in this custom Dior gown befitting the event (if ever there's a moment to go big, it's at the Oscars).
At the 2015 Critic's Choice Award
More pantsuit territory, in this case Gucci (and opting to wear the blazer as a top again, to fabulous effect). Even when it's a simple outfit, there's always an element of style and panache.
At the 2015 SAGs
Similarly, this vintage John Galliano makes sense at the Screen Actors Guild awards. It's also a nice choice away from black (which Aniston often favors).
At the Oscars, 2015
Over the years, Atelier Versace has really done right by Jen, and no more so than this Oscars gown that was semi-sheer from the waist down and covered in sparkles (Aniston: wearing simple gowns that get more beautiful the more you look at them).
At the All-Star Tribute to James Burrows, 2016
While technically not a red carpet, this event's notable for Aniston reuniting with some of her Friends costars. The five were there to pay tribute to James Burrows, who directed the series. It's hard to see the bottom of her outfit, but her satin lavender top feels perfectly right for "fancy event dinner."
At the 'Office Party' Premiere, 2016
Very, very occasionally, Aniston will go for a patterned dress, and when she does she absolutely nails it. This Roberto Cavalli is still very much in keeping with her aesthetic (bodycon but classic) but still gives some nice visual contrast with the floral pattern.
At the Vanity Fair Oscar Party, 2017
Once again Atelier Versace, this low-cut and also thigh-high split dress is both daring for Aniston and exactly in her wheelhouse. This also marks one of the last red carpet appearances for Aniston and Theroux, who amicably parted ways in 2018.
At the "Louis Vuitton Masters: A Collaboration with Jeff Koons," 2017
Aniston doesn't always go with leather on the red carpet, but this corset top is exactly the right note with her more tailored pantsuit—a very chic Louis Vuitton.
At 'Murder Mystery's 2019 Premiere
Speaking of leather! Aniston must have loved the bustier, because here she wears a full leather mini by Celine for just the right note of upscale but casual.
At the Screen Actors Guild Awards in 2020
I can't stress enough that this moment broke the Internet: The silk vintage Dior is stunning on Jen, of course, but the red carpet moment where she reunited with ex-husband Pitt (and the two were clearly delighted to see each other) set the rumor mill running once again.
At the Power 100 Women in Entertainment Event, 2021
A jumpsuit!! Even though it's a little out of Aniston's normal red carpet formula, it works: cut to the floor, with a strapless neckline and absolutely classic tailoring. Actually, I might want her to wear more jumpsuits.
At the L.A. Premiere Of Netflix's "Murder Mystery 2" in 2023
Never, ever count Aniston out for her red carpet appearances: At Murder Mystery 2's premiere, she wore this (Atelier Versace!) silver chain dress that is absolutely stunning. As per ushe, Aniston follows a familiar formula: Find a classic silhouette that she knows works, then do something a little different than what she's done in the past. It's worked for her for decades!
Stay In The Know
Marie Claire email subscribers get intel on fashion and beauty trends, hot-off-the-press celebrity news, and more. Sign up here.