Here’s What Today’s It Girls Looked Like in 2016—From Hailey Bieber to Charli XCX
- - Here’s What Today’s It Girls Looked Like in 2016—From Hailey Bieber to Charli XCX
Sophie WangJanuary 16, 2026 at 2:41 AM
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Here’s What Today’s It Girls Looked Like in 2016 Getty Images
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Chokers, band tees, ripped jeans, and berets. Halsey’s feature on “Closer” by the Chainsmokers and Justin Bieber’s “Lose Yourself.” Taylor Swift’s “girl group” era, King Kylie and Kylie Cosmetics, the debut of Stranger Things, Pokémon Go, and Leonardo DiCaprio’s first Oscar. Gigi Hadid and Zayn Malik, Kim Kardashian and Kanye West, and Miley Cyrus and Liam Hemsworth. The death of Prince and David Bowie, and, just at the tail end, the first presidential election of Donald Trump. Yes, 2016 was quite a year.
As the world reminisces on a decade past, we take a look at what some of today’s It girls were up to 10 years ago—from Hailey Baldwin and Kendall Jenner’s OG bestie style moments to Swift’s short-lived Bleachella hair and Sabrina Carpenter’s teenage fashion, to can’t-miss fits from Zendaya, Ariana Grande, Charli XCX, and Rihanna.
Ahead, see some quintessential 2016 looks from our favorite It girls.
Taylor Swift
Attending the 2016 Met Gala, with her freshly bleached hair, Swift embraced all the grunge that the year had to offer. Her blonde bob would come to define this time period for the star, representing a transitional few years between her 2014 1989 album and 2017’s Reputation—a time affectionately referred to as her Bleachella era, thanks to the star’s Instagram post from Coachella.
John Shearer - Getty Images" data-src=https://s.yimg.com/ny/api/res/1.2/PM50BtR9fbtRMQA4jyMXng--/YXBwaWQ9aGlnaGxhbmRlcjt3PTEyNDI7aD0xODY1/https://media.zenfs.com/en/aol_harper_s_bazaar_298/fa9ceb56fb6c639ac1e12ee2e3d7dc90>John Shearer - Getty Images" src=https://s.yimg.com/ny/api/res/1.2/PM50BtR9fbtRMQA4jyMXng--/YXBwaWQ9aGlnaGxhbmRlcjt3PTEyNDI7aD0xODY1/https://media.zenfs.com/en/aol_harper_s_bazaar_298/fa9ceb56fb6c639ac1e12ee2e3d7dc90 class=caas-img>John Shearer - Getty Images
Kendall Jenner
Speaking of Coachella, Kendall Jenner headed to the festival in another 2016 classic: a crochet dress. She paired the piece with strappy tassel sandals and a chunky silver necklace, and pulled her hair into two space buns on top of her head.
Bauer-Griffin - Getty Images
Kendall Jenner and Hailey Bieber
When she wasn’t at Coachella, Jenner was stepping out with Hailey Bieber (then Baldwin) in ripped denim and suede ankle boots. The two models wore their hair in matching messy buns and walked hand in hand. Jenner layered a transparent long sleeve over her Givenchy bralette and her bestie paired a tan tank with a long blue trench coat.
BG001/Bauer-Griffin - Getty Images
Kylie Jenner
Stepping out with Tyga, her boyfriend at the time, Kylie Jenner brought one of her colorful King Kylie looks out to play. With long orange-red hair, painted brows, and long lashes, the Kylie Cosmetics founder epitomized 2016 beauty, and here, she styled her glam with a fur coat, bodycon dress, and lace-up ankle boots.
Robert Kamau - Getty Images
Zendaya
Super-short hair, fitted leather jacket, lacy slip, and over-the-knee boots: Zendaya gave us a 2016 look we wouldn't be shocked to see now, in 2026 (or at least a contemporary version of). Attending the ESSENCE 7th annual Black Women in Music event, the actor looked like a total rockstar.
Jason LaVeris - Getty Images
Rihanna
Rihanna, too, made 2016 look so cool. Stepping out in New York City, the star embraced the graphic-tee trend with an off-the-shoulder oversize Tupac T-shirt and skin-tight leather pants. Her long hair was pulled into a high ponytail on top of her head, and she held two bags in one arm. On her feet were, of course, some Fenty x Puma sneakers.
Robert Kamau - Getty Images
Gigi Hadid and Zayn Malik
The 2016 It Couple matched in red, white, and blue for a coordinated September date night in New York City. Zayn Malik leaned pulled out a Rolling Stones band tee and ripped skinny jeans for the evening, while Gigi Hadid layered a fuzzy red cardigan over a white tank and ripped blue jeans. Around her waist, she tied a flannel—because it was 2016.
Robert Kamau - Getty Images
Bella Hadid
Like sister, like sister. At LAX, Bella Hadid took a page from Gigi's style handbook and tied a flannel around her waist. The rest of her ensemble was an all-black look, featuring a zip-up hoodie from her collaboration with Chrome Hearts, a classic tee, and skinny jeans ripped at the knees. Her Western-style belt, however, proved that some things never change.
starzfly/Bauer-Griffin - Getty Images
Sabrina Carpenter
Years before Short n’ Sweet and Man’s Best Friend, a 16-year-old Sabrina Carpenter attended the 2016 Nickelodeon Kids’ Choice Awards in a time capsule of a look. Her black-and-white ensemble was courtesy of Alice + Olivia, and she paired it with platform sandals and an Olympia Le Tan Alice in Wonderland clutch—a sweet foreshadow to Carpenter’s upcoming role in Lorene Scafaria’s new musical take on the beloved story.
Steve Granitz - Getty Images
Zoë Kravitz
Attending the Alexander Wang show during New York Fashion Week in September 2016, Zoë Kravitz wore a look not entirely unlike one we might see her in today. While main differences stood out—the belt choker, chunky ankle boots, and studded bag, the lacy slip itself looked like a classic—proving a LBD is always a timeless piece.
Robert Kamau - Getty Images
Kim Kardashian and Kanye West
Kim Kardashian and Kanye West were going strong in 2016, and their style was as bold as ever. Attending the Off White show during Paris Fashion Week, they held hands in clashing patterns—on her, a leopard-print coat, and on him, a marble-dye sweatshirt and trousers.
Marc Piasecki - Getty Images
Suki Waterhouse
The leather beret, the red-leather pants, the massive platform boots... Suki Waterhouse has always been that girl.
Alo Ceballos - Getty Images
Selena Gomez
For Selena Gomez, 2016 meant the Revival Tour, an emotional American Music Awards acceptance speech, and a newly-discovered love of high fashion. And this look—with its circular sunglasses, over-the-knee boots, and cut-out bodysuit—was another defining moment from the year.
Marc Piasecki - Getty Images
Ariana Grande
With the flannel, light-wash denim shorts, and boots, Ariana Grande’s on-stage look was a 2016 classic. The most recognizable part, however, was her high ponytail—a 2010s signature style she recently brought back for the 2026 Golden Globes.
Gary Gershoff - Getty Images
Miley Cyrus
At the 2016 iHeartRadio Music Festival, Miley Cyrus went full rockstar, with skin-tight leather pants, Billy Idol sunglasses, and tons of silver chains.
Kevin Mazur - Getty Images
Charli XCX
If there is one look worth recreating a decade on, it might have to be Charli XCX’s Glastonbury fit. The black-and-green floral top, orange miniskirt, and muddy Hunter boots made for an enviably cool ensemble, and her sunglasses, zipper choker, and dark magenta lip made it totally 2016.
Danny Martindale - Getty Images
Charli XCX, Again
As a bonus, here’s Charli XCX in a leopard-print beret and matching wide-leg trousers at the Royal Academy of Arts Summer Exhibition 2016. The magenta eyeshadow was absolutely perfect.
Jeff Spicer - Getty Images
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