32 Times A Jennifer Aniston Character Had On The Cutest Outfit (2025)

Jennifer Aniston has been one of the most enduring figures on our screens for the past 30 years, from her Emmy-winning breakout role as Rachel Green on the iconic sitcom Friends to her acclaimed performance as Alex Levy in The Morning Show, one of Apple TV+’s best series. And that's not to mention the actress's best movies, including slapstick comedies like We're the Millers and Horrible Bosses and beloved rom-coms like Picture Perfect and He's Just Not That into You. And along the way, Ms. Aniston has sported some majorly memorable ensembles across both the big and small screens. Here are 32 times a Jennifer Aniston character wore the cutest outfit.

Rachel's Mint-Green Dress In Friends

Rachel Green was the fashion-minded friend of the Friends bunch, which means Jennifer Aniston was regularly outfitted in some incredible clothes during the sitcom's ten-year tenure. One such ensemble was the infamous "commando" dress that Rachel eventually wears to Ross's museum function in the season three episode "The One Where No One's Ready". (One of the most ridiculous Friends episodes, the installment boasts another iconic fashion moment for the gang: when Joey ends up wearing all of Chandler’s clothes in spite.)

Tory's Blue Polka-Dotted Dress In Leprechaun

A year before she was known to TV fans as Rachel Green, Aniston had a starring role as a spoiled teenager stalked by a killer leprechaun in the 1993 low-budget horror flick Leprechaun. And while the freaky franchise is known more for its scares than its style, Jennifer's Tory still manages to make an impression with her breezy Beverly Hills looks, including this pretty blue-and-white polka-dot dress.

Kate's Perfectly '90s Outfit In Picture Perfect

One of our favorite iconic outfits from '90s movies is the workplace attire that fledgling advertising rep Kate Mosley (Aniston) sports in the 1997 rom-com Picture Perfect. It's certainly not your usual corporate get-up—instead, Kate coolly opts for a black cami dress layered over a basic tee, which she accessorizes with pigtails, tiny sunglasses and a backwards baseball had. It may get you a meeting with HR but it will have you seriously rethinking your office wardrobe.

Sarah's Satin Gown in Rumor Has It

The 2005 comedy Rumor Has It is an odd film, featuring three generations of women who are sexually charmed by the same man—and when that man is played by Kevin Costner, you can't really blame them. However icky the premise, though, the rom-com does feature some great fashion moments, including a sky-blue, body-hugging satin gown that Aniston's character Sarah Huttinger stunningly dons for a charity ball opposite Costner's Beau Burroughs.

Rachel's Schoolgirl Skirt In 'Friends'

There are so many iconic '90s outfits on Friends that it's hard to single one out, but Rachel Green did have a bit of a uniform in the early seasons, usually some kind of mock turtleneck and mini skirt situation. We love this fashionable schoolgirl take on that combo, with Rachel pairing a long-sleeved, cropped sweater with a plaid, pleated mini, knee-high socks, and chunky black shoes. It's decades later, and we'd still wear this prep-school look today!

Beth's Crisp Workwear In He's Just Not That Into You

Things may be a mess in Beth Murphy's personal life—after seven years together, Beth wants to get married, but her boyfriend Neil (played by Ben Affleck) does not—but at least she looks entirely put-together in her professional career. In the 2009 ensemble rom-com He's Just Not That Into You, copywriter Beth regularly wears crisp white button-downs and tailored treasures that, yes, are decidedly more stylish than Neil's go-to cargo pants.

Nina's Sun Hat In The Object Of My Affection

Given that the 1998 rom-com The Object of My Affection was hitting theaters at the height of Aniston's Friends fame, costume designer John Dunn wanted to do everything to make the film's leading lady, social worker Nina Borowski, look entirely different from Friends' Rachel Green, per The Los Angeles Times. And he succeeded, giving Nina a sweet, relatable—but purposefully not sleek—wardrobe of crochet sun hats, cozy cardigan sweaters and feminine floral skirts.

Polly's Boho Scarves In Along Came Polly

The 2004 romantic comedy Along Came Polly sees Aniston play the title character, easy, breezy bohemian Polly Prince, who shakes up the buttoned-up life of neurotic actuary Rueben Feffer (Ben Stiller). And the actress's wardrobe is fittingly free-spirited, stocked with silk scarves, layered jewelry, ripped jeans and tons of texture.

Rachel's Denim Vests In Friends

Sweater vests and a sarcastic wit may have helped turn Matthew Perry's Chandler Bing into one of the funniest sitcom characters of all time, but he wasn't the only Friends star with a strong vest game. Jennifer Aniston's Rachel Green also memorably sported the sleeveless look throughout the show, though she more often opted for cool denim rather than Chandler's nerdy knits.

Alex's Red Power Coat In The Morning Show

Jennifer Aniston has said that filming The Morning Show can be "so hard," but she certainly makes it look easy in Alex Levy's powerful (and sometimes nostalgia-inducing) quiet-luxury looks. One gorgeous example is the double-face cashmere red trench from Michael Kors that Aniston's Alex sports in the third episode of season one. "I've let you bozos handle this long enough," she tells a bunch of male executives while wearing the designer overcoat. "We're doing things my way." And cutting such a strong figure, you totally believe her.

Nina's Maternity Formalwear In The Object of My Affection

Looking chic while pregnant is a fashion feat, but Aniston's Nina Borowski manages to do just that in The Object of My Affection. While attending a wedding with her gay roommate turned love interest George Hanson (played by Paul Rudd, in one of his best roles), Nina drapes her growing baby bump in a dreamy, sleeveless Pea in the Pod maternity gown that costume designer John Dunn dyed from the original white to a pretty pale blue, reported The Los Angeles Times.

Rachel's Gingham Frock In Friends

The gals from Friends never shied away from a good pattern, whether Phoebe's boho florals or Monica's stylish stripes. And fashion maven Rachel Green was no exception—we especially love the gingham shift dress the character wore in the season 3 episode "The One with the Thumb." This checkered look definitely gets a thumbs up from us!

Katherine's Knit Dress In Just Go With It

Jennifer Aniston has starred alongside close pal Adam Sandler in some of his best (and worst) movies. Their 2011 collaboration Just Go with It sees the actress play Katherine Murphy, the assistant of a plastic surgeon (Sandler) who gets enlisted by her boss to pose as his ex-wife to help him woo a sixth-grade math teacher (Brooklyn Decker). She stylishly maintains the facade on a family trip to Hawaii, wearing a crochet, cream-colored Anna Kosturova dress

Brooke's Neutral Layers In The Break-Up

The incompatibility between Aniston's The Break-Up character Brooke Meyers and her soon-to-be-ex Gary Grobowski (Vince Vaughn) is evident even in their clothing choices — while she argues that he is immature and slovenly, Brooke dresses decidedly grown-up and put-together, a nod to her perfectionistic attitude. And speaking of perfect, we love this simple but chic work look, with a clean white button-down, cream short-sleeved cardigan and elegant Chanel Cerf tote.

Rachel's Farmer-Chic Overalls From Friends

Rachel Green is a city girl through and through, but the fan-favorite Friends character has been known to add some rural sweetness to her otherwise urban lifestyle, thanks to the farmer-chic overalls she regularly wears in the sitcom's early seasons. (And honestly, with that famous Rachel haircut as an accessory, she can really pull off any outfit.)

Sarah's Asymmetrical LBD In Rumor Has It

From Audrey Hepburn's iconic Breakfast at Tiffany's look to Julia Roberts's elegant Pretty Woman frock, the little black dress is a cinematic favorite. And Jennifer Aniston adds to the style's onscreen canon with the sleek, asymmetrical LBD cocktail dress from BCBG MaxAzria that the actress memorably wears in the 2005 comedy Rumor Has It.

Alex's Mock-Neck Midi Dress In The Morning Show

Aniston's The Morning Show character Alex Levy has an incredibly enviable wardrobe — she's a famous news anchor, after all, so she always has to be camera-ready. And she certainly is in this long beige knit dress from Jil Sander; we especially love the way the front pocket detailing adds depth and interest to the otherwise simple silhouette.

Rachel's Mod Mini Dress In Friends

The early part of the 1990s saw the resurgence of many fashion trends from the '60s and '70s, a revival that made its way onto Friends courtesy of Rachel Green's closet. The stylish TV character frequently sported mod-inspired miniskirts, knee-high boots and geometric minidresses in the sitcom's early seasons — this bold black-and-white number from the show's second season is a memorable example.

Audrey's White Fur Coat In Murder Mystery 2

Even in the middle of a kidnapping, Aniston's Audrey Spitz manages to turn a look — throughout the Netflix sequel Murder Mystery 2, the former hairdresser-turned-detective wears such bold and eye-catching looks as beaded lehengas, lacy minidresses, statement jewelry and, in the above scene, an off-white ostrich feather coat with oversized gold hoop earrings.

Debbie's Silk Blouse In 'Til There Was You

Not everything is as perfect as it seems on the surface in the marriage and home of successful doctor Debbie, Aniston's character from the 1997 romance 'Til There Was You. But it certainly looks that way at least, with Debbie forever dressed impeccably in chic silk blouses, preppy pearl necklaces and an elegant updo.

Brooke's Little Black Dress In The Break-Up

Few outfits are as classic, chic and commanding as the little black dress. It's the perfect outfit for a big dinner party with friends and, apparently, a heart-crushing fight with your lover. Aniston surprisingly wears this strappy LBD to both events in The Break-Up, paired with a simple Cartier watch. If you have to end things with a longtime love (in this case, Vince Vaughn's Gary Grobowski), at the very least, look great doing it

Mickey's '70s Blouse In Life Of Crime

In the 2013 black comedy Life of Crime, an Elmore Leonard adaptation, Aniston plays Margaret "Mickey" Dawson, the wife of a corrupt real-estate developer who gets kidnapped by two criminals who want inside information about her husband's crooked business. With the movie set in the 1970s, Mickey's wardrobe is fittingly groovy, all giant sunglasses, neck scarves, polyester fabrics and patterned blouses.

Katherine's White Dress And Statement Belt In Just Go With It

In the 2011 romantic comedy Just Go with It, Aniston looked every bit the stylish California girl in a cream body-con dress, a beige statement belt and strappy nude sandals during a night out at a Beverly Hills hotspot. In the Happy Madison Production, the actress plays Katherine, an office manager who ends up pretending to be married to her best friend and co-worker, played by Adam Sandler.

Alex's Cozy Sherpa Coat In The Morning Show

On The Morning Show, Aniston's Alex Levy ushered in the second season of the Apple TV show in style. In the premiere episode, the famous news anchor was decked out in a faux shearling Kylie Coat by Stand Studio, a long white teddy coat that is very much in line with the character's designer wardrobe of simple and comfortable but extremely high-quality luxury pieces.

Kate's Green Dress In Picture Perfect

In a crowd of black, beige and navy suits, Jennifer Aniston's ambitious yet casually dressed Kate Mosley definitely stands out in her advertising career. ("We dress for the job we want, not for the job we have,” advises Kate's colleague in one scene.) And while, yes, this bright-green, body-hugging lace dress would immediately warrant a meeting with HR, it certainly makes her the most memorable employee in the office.

Rachel's Color-Block Turtleneck In Friends

There were sweaters and turtlenecks galore during the decade-long tenure of Friends — it was the '90s, after all — but few wore them as well as Rachel Green. A go-out outfit for Jennifer Aniston's iconic sitcom character was a slim-fit roll neck (like the above cream-and-crimson color-blocked number), tucked into a black mini skirt with matching tights.

Alex's Pinstriped Suit In The Morning Show

Alex Levy doesn't often wear power suits on The Morning Show — instead, "we did trousers and sports coats. We wanted her to be sophisticated, but we also wanted her to be accessible and culturally appropriate," Aniston's stylist Clare Hallworth told Entertainment Weekly . However, when she does suit up, she makes quite the impression, like in this perfectly tailored, pinstriped number by Dolce & Gabbana.

Olivia's Paisley Blouse In Friends With Money

In Nicole Holofcener’s low-key female-centric comedy, Aniston plays Olivia, a California woman who takes up house cleaning after leaving her lucrative job, a status change that prompts some awkwardness among her more successful and wealthy friends (Joan Cusack, Frances McDormand and Catherine Keener). She may be worried about her finances, but Olivia looks like a million bucks in her pretty-in-pink paisley top.

Eloise's Sweater Dress In Love Happens

As Eloise, a creative floral designer who owns a flower shop, in the 2009 romantic drama Love Happens, Aniston's character warms up from the rainy Seattle weather in a parade of cozy knits — like this great green cardigan dress, which she accessorizes with a black belt and gold jewelry — floppy beanies, leather gloves and colorful scarves.

Mickey's Groovy Beret And Leather Jacket In Life of Crime

As Elmore Leonard in Life of Crime, Jennifer Aniston looks criminally cool in the comedy's 1970s wardrobe. In one striking monochromatic look, Aniston's character caps her bleach-blonde blow-out with a patterned brown beret, which perfectly pairs with her caramel-colored leather coat and mocha-hued handbag. Elmore's circumstances aren't ideal — she gets kidnapped due to her spouse's job, but hubby refuses to pay the ransom to get her back — but at least her clothes are!

The annual Thanksgiving episodes on Friends are some of the sitcom's most beloved installments, one of which sees the gang playing a friendly game of touch football known as the "Geller Bowl" in season 3. Along with the hilarious athletic hijinks, the game is memorable thanks to Rachel's sporty-cute football uniform of a backwards baseball cap, braided pigtails, layered tees and cozy sweatpants.

Rachel's Sheer Collared Shirt In Friends

For three decades, Rachel Green has continued to have one of the most enviable wardrobes on television — really, could she be any more fashionable? One of our favorite looks that the character sported throughout the 10 years of the NBC sitcom is this sheer gray shirt, which is given some unexpected interest with its black contrast neckline and triangular point collar.

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