A screen darling since becoming Rachel in Friends, Jennifer Aniston has had a career and style evolution that would be the envy of anyone: first coming to prominence as an actor in the 1990s, then quickly rising to fame, and literally decades of interesting TV and film projects. And lucky for us, she has a cool, fun presence on the red carpet, usually opting for a chic, simple style (though, as we'll see below, sometimes she takes big fashion risks). Over the course of her career, she has had some great moments. Over the years, people have really, really cared about who Aniston is dating or married to. Aniston knows how to communicate about her love life well enough to entertain us, but she never shares too many details.

Keep scrolling for Aniston's fabulous dress, a peek into her love life, and a great combination of both.

Aniston made several television appearances in the 1990s, playing Jeannie Buehler on NBC's Ferris Bueller (based on the movie, naturally). In this NBC party, one of her first event photos, she is casual in denim, a gray satin shirt, and casual wavy hair.

Here she is with co-star Charlie Schlatter, who played the main character Ferris Bueller on the show. (They dated briefly.)

At a casual NBC party in 1990, Aniston wears a black tank top, chunky belt, and maxi skirt that is very 90s. Despite the more formal things to come for her, I love seeing early Jen dressed in teen-appropriate casual attire.

As soon as Friends debuted in the fall of 1994, the cast members became celebrities almost overnight. This photo of each actor holding a Central Perk-worthy coffee mug was one of the first event photos taken after the series began its meteoric rise to fame.

At one of the first awards ceremonies, Aniston, along with stars Matthew Perry and David Schwimmer, sported the famous early "Rachel" hairstyle.

Aniston kept it simple in a black tank dress for the event. (Friends won the People's Choice Award for Favorite New TV Comedy Series.)

At the time of this 1999 premiere, the gossip magazines were buzzing: "Are Aniston and Brad Pitt, arguably the two most popular actors alive, actually dating?" This was their first red carpet event, and it was clearly confirmed yes! This was their first red carpet event together, and the answer was a resounding yes. Aniston, as always, is simple, chic, and aesthetically pleasing, but still wears fun separates with a slit in the middle of her shirt.

Whoever created this particular gown is unknown, but at this point Aniston is beginning to become the red carpet style she will be known for her entire career. Even more puzzling is the "relaxed beach wave" she is doing.

Aniston doesn't always lean on color, but when she does, it's exceptional. This simple red Prada column gown (with a small bag and matching red lips to keep things simple) has become one of her most iconic early outfits.

Once again utilizing her husband as her best accessory, Aniston steps into the pantsuit here. She often favors gorgeous dresses, but here the blazer (worn as a top) is just the right amount of chic. I'm not crazy about the sunglasses, but oh well.

Proving that simplicity is often the key to her fabulous red carpet style, Aniston's simple Chanel dress was considered one of the best Emmy dresses ever.

In vintage Valentino, Aniston went bold (and in a rare moment of daring).

Likewise, this beaded halter-top Versace gown (worn to support Pitt's film premiering at Cannes) is not over-the-top in terms of color or detail, but that's what brilliant simplicity is all about.

Frankly, Aniston's casual style is as great as the haute couture red carpet (this simple blazer and denim would work just as well today). Not so fun: In May of this year, rumors began to circulate that Pitt and co-star Angelina Jolie might be romantically involved. This photo was taken in October; Aniston and Pitt would officially divorce in March 2005.

We're now into the "short, sparkly, and utterly fabulous" part of the slideshow (and frankly, she deserves it). I love this metallic slip dress, especially the fact that it's out of the colors she always chooses for red carpet couture. (Although they never posed together, Aniston was dating co-star Vince Vaughn.)

One more thing. The slip dress appears to be made of hammered gold, but I forgot how good this color looks on her. At this event, Aniston joked about her love life and work life running parallel: "If I had a project titled 'Eternal Love with a Stable Adult Man,' I would be at table 6 and my agent would be at table 12." [This pink Christian Lacroix dress may be one of the most fun things she's ever worn. (And your memory is correct: yes, Aniston and Gerard Butler dated briefly.)

I love this Kaufman Franco mini dress. It's mini, it's plunging, it's sparkly, and she couldn't look better in it. a++.

First, this Prada print dress is amazing and I wish she would wear it more (she reused it at least once). Second, this was Aniston's first official red carpet event in which she appeared with her husband-to-be Justin Theroux, who was clearly having a blast in the audience.

If you're going to sign a bottle of perfume with your name on it, you might as well dress in this gorgeous Vivienne Westwood. I firmly believe that Aniston should always wear these colors.

Like I said, when Aniston wears color, she does it right: in this custom-made Dior gown befitting the event (if there is ever a moment to go big, it is the Oscars).

And then there is the realm of the pantsuit, in this case Gucci (and the blazer is worn as a top again, to great effect). Even in simple attire, there is always an element of style and glamour.

Similarly, a John Galliano of this vintage makes sense for the Screen Actors Guild Awards. It is also a nice choice away from black (which Aniston often favors).

Over the years, Atelier Versace has really gone all out for Jen. Nothing more so than this Academy Award gown, semi-sheer from the waist down and covered in glitter (Aniston: wear a simple gown that becomes more beautiful the more you look at it).

Although not strictly a red carpet event, the event was notable for reuniting Aniston with her "Friends" co-stars. The five were there to pay tribute to James Burrows, who directed the series. The bottom of her outfit is hard to see, but her satin lavender top looks perfect for a "lavish event dinner."

Every once in a while, Aniston tries on a patterned dress, and when she does, she absolutely succeeds. This Roberto Cavalli dress follows her aesthetic (bodycon yet classic), but with a contrasting floral pattern.

Again, this low-cut, thigh-high split dress from Atelier Versace is bold for Aniston and right up her alley. This was also the last red carpet appearance for Aniston and Theroux, who parted amicably in 2018.

Aniston doesn't always pair leather on the red carpet, but this corset top goes perfectly with her tailored pantsuit.

Speaking of leather. Aniston must have loved the bustier. Here, she is wearing a full leather mini from Celine, which is both luxurious and casual at the same time.

We can't stress enough how this moment took the Internet by storm: the silk vintage Dior is, of course, perfect for Jen, but the red carpet moment when she reunited with her ex-husband Pitt (and they were clearly happy to see each other again), the rumors ran again.

Jumpsuits. It's a bit of a departure from Aniston's usual red carpet conventions, but the floor-length cut, strapless neckline, and absolutely classic tailoring pay off. In fact, I might wish she wore more jumpsuits.

Never count on Aniston's red carpet appearances: at the premiere of Murder Mystery 2, she wore this (Atelier Versace) silver chain dress. As always, Aniston follows a familiar formula: find a classic silhouette she knows and do something a little different than she has done in the past. It has worked for her for decades.