Shiloh Jolie-Pitt's Most Stunning Red Carpet Looks

As the daughter of Angelina Jolie and Brad Pitt, Shiloh Jolie-Pitt was born into Hollywood royalty. Despite possessing that famous hyphenated name, however, Shiloh Jolie-Pitt opts to lead an under-the-radar life and rarely makes public appearances. Her furtive and media-shy persona makes it all the more special, then, when she decides to accompany her A-list mom to red carpet events, showcasing her quirky sense of style.

Having reportedly distanced herself from dad Brad Pitt with a name change, Jolie-Pitt is proving to be a headstrong and fiercely independent young person. That independence is reflected in her approach to red carpet fashion, with the celeb progeny wearing a number of dazzling looks over the years. As a child, Jolie-Pitt was famed for her snazzy gender-neutral garb, an aesthetic that led to mom Jolie requesting the public to kindly stop making such a big deal out of her daughter's sartorial preferences. "Some kids wear capes and want to be Superman and she wants to be like her brothers," Jolie told the Daily Mail. "It's who she is. It's been a surprise to us and it's really interesting, but she's so much more than that — she's funny and sweet and pretty. But she does love a tie." Since then, Jolie-Pitt has stunned in all manner of incredible outfits. Let's take a look at them with Shiloh Jolie-Pitt's most stunning red carpet looks.

According to body language experts, Shiloh Jolie-Pitt has a close relationship with her mom, and this is evident in Angelina Jolie's support of her child's unique approach to fashion. Back in 2014, 8-year-old Jolie-Pitt made her red carpet debut, appearing with her dad, Brad Pitt, and older brothers, Maddox and Pax Jolie-Pitt, at the premiere of "Unbroken." In one of her most iconic red carpet moments, she donned an adorable suit and her hair was slicked back. She looked equal parts mom and dad in her first stint in the spotlight, her hairdo channeling a young Pitt circa "Meet Joe Black" and her features resembling mom Jolie when she herself appeared on the red carpet as a child. The elementary schooler's style was on point: At the time, there was a rise in female celebs wearing suits to high-profile events, including Jolie-Pitt's mom, who sported a tux at the BAFTAS earlier that year.

Jolie was incredibly attentive and respectful of her daughter's decision to don gender-neutral garb. Four years earlier, she was asked to address her daughter's sartorial preferences in a chat with Vanity Fair. "Shiloh, we feel, has Montenegro style," she enthused. "It's how people dress there. She likes tracksuits, she likes [regular] suits. So it's a suit with a tie and a jacket and slacks, or a tracksuit ... She likes to wear boys' everything. She thinks she's one of the brothers."

By 2017, Shiloh Jolie-Pitt had grown significantly since her last red carpet appearance and had also changed up her style. Appearing at the the premiere of "The Breadwinner" at the Toronto International Film Festival with her mom, Angelina Jolie, and siblings Zahara, Vivienne, and Knox Jolie-Pitt, Shiloh looked effortlessly cool. Then aged 11, she channeled classic '90s grunge chic in an oversized gray flannel shirt, which was worn open over a black sweater and jeans ensemble. The outfit was topped off with a unique necklace.

Shiloh looked like a mini Kurt Cobain in the cute 'fit and the styling was on-trend for the era. Though the 2020s are firmly entrenched in a Y2K resurgence, the '90s aesthetic was all the rage the previous decade. In the 2010s, everyone from Hailee Steinfeld to Charli XCX donned oversized plaid on the red carpet, proving that Shiloh has been a consummate fashionista from a young age.

The Jolie-Pitt kids have evidently learned a thing or two about mastering red carpet style from their glamorous parents. Appearing at the premiere of "First They Killed My Father" at the Toronto International Film Festival in 2017, Angelina Jolie's six kids had a delightful matching moment. Taking a break from her usual all-black outfits, Shiloh Jolie-Pitt stunned in a smart black and white suit. The outfit was topped off with a waistcoat, which added a fun retro element to the classic look. She sweetly matched with Pax, Vivienne, and Knox Jolie-Pitt, who all wore suits to the premiere.

It was a particularly difficult time in the youngsters' lives, as their parents were in the midst of a divorce. But speaking to Vanity Fair that year, Jolie said that she was doing everything she could to ensure that her children's lives remained relatively normal amid the highly publicized split, and in turn, received the support they needed. "I do not want my children to be worried about me," she said. "I think it's very important to cry in the shower and not in front of them. They need to know that everything's going to be all right even when you're not sure it is." And, as evidenced by their warm rapport on the red carpet, the wholesome siblings were supporting each other, too.

Angelina Jolie and her kids continued to show their support for "The Breadwinner" in the fall of 2017. The A-lister appeared with daughters Shiloh and Zahara Jolie-Pitt at the TCL Chinese 6 Theatres in Los Angeles, where Jolie also gave a talk championing the feminist themes of the aforementioned Afghanistan-set animated film. "There are few countries in the world where it is harder to be a young girl, where barriers between girls and their dreams and their rights are so high and so painful to experience and observe," she said at the fest, per Variety.

Accordingly, Shiloh wore a suitably gender-nonconforming ensemble for the occasion, donning an all-black suit and matching sneakers. Once again, she accessorized with a statement necklace, as well as a black backpack, which added a touch of youthfulness to the otherwise mature look. Zahara also wore black for the event, with the sisters contrasting perfectly against their mom's stunning white dress.

Shiloh Jolie-Pitt enjoys a close relationship with her siblings, and has a particularly strong bond with sister Zahara Jolie-Pitt. The siblings kicked off 2018 in style, and had a wholesome twinning moment while supporting mom Angelina Jolie at the National Board of Review Awards Gala in New York. It was a stylish family affair; while Jolie wore a draping, gothic-inspired gown, her kids were dressed up in power suits. Shiloh looked chic in an '80s-style oversized black and white tux, and her slightly spiky short hair added a punky twist to proceedings. 

Meanwhile, Zahara, who usually wears dresses on the red carpet, matched her sister's vibe in a similarly retro pants suit. The siblings looked incredible as they lent their own special iterations to the almighty power suit. However, Shiloh's ensemble came with an unexpected accessory: an arm brace. The youngster had broken her arm and collarbone while snowboarding during a family vacation in Lake Tahoe, but was reported to be swiftly on the mend.

Though Shiloh Jolie-Pitt has become the spitting image of mom Angelina Jolie, she was previously her father's doppelgänger. In 2018, Shiloh once again joined her mom and elder sister, Zahara Jolie-Pitt, on the red carpet, this time at the Annie Awards. Gone were Shiloh's floppy blond locks; this time she sported a semi-buzz cut, which resembled the 'do her father famously debuted when he starred in "Mr. & Mrs. Smith" (which, incidentally, is the movie that brought Shiloh's A-list parents together). Her newly trimmed mane was complemented by a black suit and white shirt combo. She completed her look with black sneakers, which added a contemporary Gen-Z twist to an otherwise conventional, albeit dapper, outfit.

It was a successful night for Jolie and her brood, with the actor-turned-producer winning the award for Best Animated Independent Feature alongside her producing colleagues. Jolie's decision to take her two eldest daughters to events related to "The Breadwinner" was seemingly reflective of her mission to instill progressive ideals in the girls (earlier that year, the socially-conscious Shiloh and Zahara asked if they could join their mom on a trip to Jordan to meet Syrian refugees).

Appearing together on the red carpet at the "Dumbo" premiere in 2019, Angelina Jolie's kids were all smiles as they lovingly supported their mom. At the time, sources told Hollywood Life that the actor's children were helping her through a difficult time. "She went through a lonely phase after her split with Brad, but has gotten over it thanks to the love and attention from her kids," a source said. "She is not ready to date or get serious with anyone until her divorce with Brad is finalized. Until then, she will continue to make her kids and her work her focus."

Shiloh Jolie-Pitt opted for a black zip-up hoodie worn over a crisp white shirt, complete with comfy black slacks and matching sneakers. Meanwhile, Zahara Jolie-Pitt donned an elegant gown and platform ankle boots, while Knox and Vivienne wore casual yet smart outfits. The contrast of Zahara's hyper-femme, glittery gown and Shiloh's gender-neutral drip perfectly encapsulated the pair's differing personal aesthetics, while simultaneously complementing one another. Moreover, the casual outfit was a welcome change for Shiloh, who had (for the most part) dressed up in classic suits at previous red carpet events. Indeed, the 'fit was youthful and fun, making it a fitting look for the premiere of a kids' flick.

By the fall of 2019, Shiloh Jolie-Pitt was once again experimenting with different styles. Though Angelina Jolie had previously told Vanity Fair that her daughter was all about suits, Jolie-Pitt was slowly shifting toward a more street style-focused aesthetic. This was none more apparent than when she attended the premiere of "Maleficent: Mistress of Evil," the second installment of the Disney franchise, and wore an oversized leather jacket. She paired the stylish piece with a white shirt, black pants, and some trendy sneakers. The teen looked like a mini James Dean with her slicked-back hair and super cool leather drip.

Prone to enjoying a themed 'fit or two, her outfit was perfectly on-point for the occasion; the moody aesthetic corresponded with the themes of the dark fantasy flick, in which her mom plays the ominous title character. Interestingly, Jolie-Pitt was originally set to star as the young Aurora in the first "Maleficent" flick, but turned it down as she felt ill-suited to the girly role (the part ultimately went to her sister, Vivienne Jolie-Pitt). "I asked Shiloh about being Aurora, and she laughed in my face. She said she'd be a horned creature," Jolie told Elle, while noting that she'd much prefer her kids don't pursue acting careers themselves.

Over the years, Shiloh Jolie-Pitt's style has evolved drastically, with the teen evidently having fun playing around with different aesthetics. In 2021, the 15-year-old appeared at the "Eternals" premiere in a unique, asymmetrical beige dress. She paired the number with cream ballet flats and simple accessories, including a practical black watch. It was her first time wearing a dress on the red carpet, with some tabloids needlessly making a big deal out of her new sartorial venture.

Though the dress was a fashion first for Jolie-Pitt, the unconventional design still encapsulated the teen's idiosyncratic approach to red carpet style. Moreover, the dress was an ode to the transformative nature of sustainable fashion, being an upcycled version of a Gabriela Hearst dress Jolie had worn at a previous event (Jolie-Pitt's siblings were also decked out in upcycled pieces at the event, with Zahara Jolie-Pitt reportedly re-wearing her mom's 2014 Oscars gown). "My kids are all mixed with vintage, and in my old Oscars dress. We did all vintage and upcycled my old stuff," Jolie told Entertainment Tonight. Following in her mom's footsteps — Jolie has long been a proponent of ethical fashion — Jolie-Pitt was making an important statement on the red carpet, and looking wonderfully stylish to boot. We stan a sustainable queen.

Shiloh Jolie-Pitt returned to her love of black attire at a red carpet event for "Eternals" at the Rome Film Fest in 2021. This time, however, she swapped the suits for a classic little black dress by Versace. Styling the dress with a sophisticated fishtail bun and gold earrings, Jolie-Pitt exuded old-school Hollywood glam. But it wouldn't be a Shiloh Jolie-Pitt outfit if the teen didn't sprinkle a dash of her idiosyncratic flair into her ensemble. 

Accordingly, she completed the 'fit with a pair of black and yellow, leopard print high-top sneakers. She was praised for the unconventional sartorial move, with Today declaring that her shoes stole the show at the glitzy event. The shoes were a fun addition to the elegant outfit, allowing Jolie-Pitt's personality to shine through. What's more, it's all too common for kids to dress like mini adults on the red carpet, with Jolie-Pitt's kitschy twist on haute couture unashamedly allowing her to express herself in a distinctly teenaged manner.

Looking more like her mom each day, Shiloh Jolie-Pitt channeled Angelina Jolie in more ways than one at the "Eternals" London premiere in 2021. In addition to serving Angelina's face at the star-studded event, the teen re-wore the stunning printed Dior dress that her mom had worn to a press conference for "Maleficent: Mistress of Evil" two years earlier. This time, however, the dress was shortened and reconstructed to fit Jolie-Pitt. She paired the dress with some simple black ballet flats and wore her hair in a bun, proving herself a pro at no-fuss red carpet styling.

It was another admirably sustainable moment for Jolie-Pitt, and a wholesome one at that. A couple of days before the event, Jolie told E! News that she not only loves sharing her clothes with her kids, but she positively encourages them to do so. "I'm like, 'Oh my god, wear it and wear it better than me! Take it, it's your turn,'" she enthused. "I'm that mom."

Continuing her red carpet winning streak, Shiloh Jolie-Pitt rocked yet another fashionable look during a visit to the Museum of Tolerance in Los Angeles in 2021. Accompanying her mom Angelina Jolie, brother Pax Jolie-Pitt, and French street artist JR to the premiere of the documentary "Paper & Glue," Shiloh looked super trendy in a blue jeans and black hooded sweater coordinate.

The outfit recalled some of Shiloh's earlier gender-neutral looks, but now a teen, she put a quintessentially Gen-Z spin on her regalia, wearing ripped jeans and distressed converse. At the time, ripped jeans — once thought to be a relic of the early 2000s — were making a major comeback. Rocked by Instagram fashion girlies and A-list celebs alike, the trend was hailed as one of the most popular jeans styles of 2021. Evidently, Shiloh is attuned to the contemporary fashion climate, but she's always keen to adopt those trends in her own quirky way, in this instance pairing the jeans with a punky hoodie complete with metal hole detailing.