Composite: Getty Images
In just a few short months, Olivia Rodrigo went from Disney darling to international pop sensation. Her debut album, SOUR, put her on the map as a rising trailblazer and GUTS only further cemented her status as one of our generation's biggest pop stars. And with her powerful, beautifully painful voice also comes a unique style and sense of fashion. From tunes to threads, she is the ultimate full package.
Before the perfectly plaid ensembles, knee-high platform heels, and custom Dior runway moments, Olivia Rodrigo experimented with her style just like all of us until she found the aesthetic that perfectly fits her unique vision. Here, we take a trip down memory lane to relive her complete style evolution – from today to 2015. (If you want to see her Met Gala looks, we've got you covered here.)
April 2024
Olivia Rodrigo has been delivering looks onstage during her GUTS world tour, where she notoriously wears a different DIY tank top every night, but she is also keeping the rock star vibes going on the streets. For a night out in NYC before heading to Europe for the tour, Rodrigo opted for a sheer LBD paired with a classic red leather jacket for a pop of color and some distressed combat boots.
April 2024
In between schedules, Rodrigo opted for a more incognito, comfy 'fit, which she completed with a pair of Sambas and a black beanie.
April 2024
While out and about with bestie Conan Gray in NYC, Rodrigo stayed faithful to her tried-and-true outfit formula, opting for a pair of Dr. Martens brogues worn over white calf socks and sheer black tights, a plaid mini skirt, and a graphic tee.
April 2024
Also in NYC, she committed to the warm and cozy aesthetic with her trusty Jadon boots and a black JW Anderson bag. If you have accessories this good, you can just keep the rest simple.
February 2024
At the 2024 Grammys, Rodrigo stunned by wearing an archival gown from Versace's 1995 spring collection, which meant the piece was older than her.
February 2024
When it came time to perform her song “vampire,” Rodrigo changed into her Docs and a fitting satin red maxi dress from Indian-American designer Naeem Khan.
January 2024
Rodrigo had a bit more fun with her style to attend a The Hunger Games: The Ballad of Songbirds & Snakes reception in Los Angeles, donning a polka-dotted, silk wrap dress from Alessandra Rich and pointed patent flats with a slicked-back hairdo.
January 2024
Rodrigo linked up with Tate McRae for a Lakers game in L.A. wearing a Norma Kamali button-down vest mini dress from the '90s over a white tee and chunky loafers from UNIF paired with white socks.
January 2024
Did someone say timeless glamour? Attending the Oscars, Rodrigo opted once again for a simple yet effective formula, pairing an archival Yves Saint Laurent tube gown with a bold lip.
December 2023
During her stint as musical guest on SNL, Rodrigo performed “all-american b*tch” wearing a pale pink mini dress with knee-high socks and Dr. Martens boots. While the visible part of the 'fit was already 10/10, she took it to the next level unveiling a cheeky message on her underwear post-show.
December 2023
Before appearing on SNL, Rodrigo also had an appearance on The Tonight Show starring Jimmy Fallon, where she opted for a coquette look comprised of a ShuShu/Tong LBD complete with blue floral motifs and some Mary Jane pump from Christian Louboutin.
December 2023
Rodrigo also kept the black dress with floral prints vibes going at the Variety Hitmakers Brunch in Hollywood wearing Carolina Herrera and ShuShu/Tong shoes.
December 2023
Rodrigo made a case for LRDs at iHeartRadio z100's Jingle Ball 2023, opting for a vintage Versace dress from the brand's 1996 archive paired with the Dr. Martens 1B60 Bex Pisa leather knee-high boots.
December 2023
To perform at the same event, she later changed into a silver mini dress from Rabanne.
December 2023
You can never go wrong with a textured baby tee and flared black pants, and this NYC outing proves that.
November 2023
Olivia Rodrigo was on cheer duty during a game between the USC Trojans and the UCLA Bruins in Los Angeles, wearing a Trojans sweatshirt, jeans, and Docs.
November 2023
Olivia Rodrigo attended the 2023 GQ Men of the Year event in Los Angeles wearing a fringe LBD from Tom Ford and platform-heeled sandals from Valentino, which showed off her black pedi.
November 2023
She rewore the same shoes to attend the 38th Annual Rock & Roll Hall of Fame induction ceremony at Barclays Center in New York City, swapping the LBD for a Valentino halter-neck option with a rose detail.
November 2023
While performing at the event, she slipped into a pair of tiger-print pants and a black tank top.
November 2023
For the premiere of The Hunger Games: The Ballad Of Songbirds & Snakes in Los Angeles, Rodrigo opted for a custom dress from Rodarte covered in black sequins and featuring a floral neckline.
October 2023
During an appearance on Jimmy Kimmel Live!, Rodrio opted for a Coach lavender mini dress paired with By Far silver sandals and matching hoop earrings.
October 2023
While promoting GUTS, Rodrigo surprised fans with an intimate performance at the Grammy Museum in L.A. wearing silver Coach loafers, pinstripe gray pants, and a lavender knit top.
September 2023
If you thought this dress Rodrigo wore to a GUTS pop-up in NYC had major ‘90s vibes, you’d be right because it's a vintage Betsey Johnson confection from that era.
September 2023
Olivia Rodrigo wore a red and white shirt with Angelina Jolie's face on it from NYC-based brand Hellcat! paired with a pleated white skirt, white socks, and Miu Miu penny loafers for the ultimate cool-girl ensemble.
September 2023
For the 2023 MTV VMAs, Rodrigo opted for a custom-made Ludovic de Saint Sernin dress covered in Swarovski crystals.
September 2023
While performing at the event, she changed into a two-piece red set comprised of a pleated mini skirt and a bra top, which she paired with Converse sneakers and white leg warmers.
September 2023
She was clearly feeling leg warmers around this time because she wore another pair, this time black over Dr. Martens, during an appearance on the Today show. She paired them with a gray set from REMAIN.
August 2023
Rodrigo started her GUTS promotions strong on the other side of the pond wearing a ‘60s inspired monochromatic white ’fit consisting of a mini knit dress by Patou and knee-high boots by LOQ.
August 2023
Who can't forget Rodrigo's night out with Heartstopper star Joe Locke? The duo attended an event for The Face Magazine in London, where the singer chose a Magda Butrym halterneck mini dress and Manolo Blahnik mules for the occasion.
August 2023
For another night out in the British capital, she kept things much simpler with light-wash jeans, a black tee, and matching Tabi ballerina shoes.
August 2023
Also in London, Rodrigo wore a Pat Benatar concert tee paired with a Sandy Liang mini skirt and LABUCQ patent Mary Jane brogues over white socks.
July 2023
During a visit to SiriusXM, Rodrigo wore a butterfly knit tee by Acne Studios paired with an Aya Muse pleated skirt and the Jimmy Choo Elisa leather pumps.
June 2023
For a YouTube event in Los Angeles promoting “vampire,” Rodrigo opted for a silk LBD with bow details by Brandon Maxwell and black patent leather pumps by Valentino.
May 2023
Rodrigo attended a Met Gala after party wearing a vintage Chanel dress from 1994.
April 2023
She might love her Dr. Martens for days off, but these Converse All-Stars come a close second.
March 2023
Olivia Rodrigo attended the 2023 Vanity Fair Oscar Party, making a case for leopard print in her custom Valentino dress.
March 2023
To attend a Los Angeles Lakers game with her friend Iris Apatow. Rodrigo wore a pair on simple loafers with a sheer long-sleeved black shirt and some funky pattenered pants.
March 2023
For the 2023 Billboard Women in Music red carpet, Olivia went for a very Y2K look with a skintight tube top and low-rise pants. She kept the look simple and skipped major accessories, sporting – and this is where a major twist comes in – a horse graphic on her pants instead.
February 2023
Olivia Rodrigo attended the Universal Music Group's Grammy after party rocking a sequined black dress with a keyhole cutout from 16Arlington. She paired the LBD with some peep-toe platform heels and a black mani. Simple but effective.
February 2023
For the actual Grammys, Olivia hopped on the sheer trend by wearing another simple but effective black dress. The piece, described as a silk georgette gown, was custom-made by Miu Miu and was paired with black satin underwear and a Tiffany & Co. statement pendant necklace for the occasion.
February 2023
Just a day after Paco Rabanne's death was announced, Olivia attended the Clive Davis pre-Grammys gala wearing a mini dress from the Spanish designer's brand's spring 2014 ready-to-wear collection. The all-leather maroon number featured a daring slit on the side.
November 2022
Olivia made the case for sheer stockings at the 37th Annual Rock & Roll Hall of Fame Induction Ceremony at Microsoft Theater, pairing hers with some suspenders, a mini skirt, and Mary Jane pumps. Her full look was ShuShu/Tong.
November 2022
Backstage, however, she traded the ensemble for a much comfier option.
October 2022
Rodrigo attended the Givenchy in Paris wearing an all-white 'fit that combined lace and satin.
September 2022
Rodrigo graced the red carpet at the 2022 Canadian Songwriters Hall Of Fame Gala in Toronto wearing… PJs? Essentially yes — expect this lace and satin set is from Saint Laurent and costs almost $5K. Instead of a just-rolled-out-of-bed look, Rodrigo opted to give her lingerie look a high glamour twist, opting for a red lip, a matching black lace choker, and strappy heels.
August 2022
While out and about in NYC, a bare-faced Rodrigo was seen sporting her trusty Dr. Martens Jadon boots, a tartan skirt from Tripp NYC, and a very Y2K-esque baby tee from UNIF. She kept the accessories to a minimum with a pair of thin silver hoops.
August 2022
When it comes to corsets, no one does it like Vivienne Westwood. Olivia Rodrigo knows this well. On August 24, the singer took to the stage at Madison Square Garden to perform Deja Vu" and "Uptown Girl" alongside Billy Joel, wearing a vintage black leather corset from the British designer, sourced from Tab Vintage. The velvet corset is part of the brand’s Fall 1991 collection, which marked the first time Westwood showed in Paris — making the piece all the more coveted. (And, yes, this Vivienne Westwood is roughly 12 years older than Rodrigo herself!)
Though the corset was undoubtedly the star of the (fashion) show, Rodrigo completed the grunge-inspired look with a distressed mini skirt from Saint Sintra, sheer black tights, lace-up combat boots, a thick black choker, and a matching hair bow.
August 2022
Rodrigo embraced the pajamas as outfits trend with this LBD. The all-black slip gown featured lace detailing along with very thin spaghetti straps. She paired the mini dress with matching loafers and white socks.
July 2022
Rodrigo attended the premiere of season 3 of High School Musical: The Musical: The Series, where she reunited with Johsua Bassett, wearing an LBD with cutout and transparencies from Nensi Dojaka and a leather choker by Christian Dior.
June 2022
Rodrigo attended the 2022 MTV Movie & TV Awards, donning a vintage dress from Jean Paul Gaultier.
May 2022
Rodrigo was a Versace girl at the Met Gala 2022, continuing the strike even at the after parties.
April 2022
At the 2022 Grammys, Rodrigo rocked a custom gown by Vivienne Westwood covered in Swarovski crystals with black opera gloves.
April 2022
To perform, she slid into her boots and a ruffled dress by Givenchy over fishnet tights.
April 2022
For a while, we have seen celebs the likes of Megan Fox and Kylie Jenner wearing bras as a top and now Rodrigo is hopping on the trend — kind of. In a recent photo dump posted to her Instagram, Rodrigo included a photo in which she is seen rocking her take on the trend.
While we are not entirely sure if Liv's is a bra — it looks more like a cropped, tiny cardigan — the effect is pretty much the same. Of course, for balance, Rodrigo paired the top with tiny sunglasses, a leather blazer, her trusty Chanel bag, an asymmetric plaid skirt, Dr. Martens, leg warmers, and an iced matcha latte. Icon behavior.
March 2022
Rodrigo attended the Billboard Women in Music event in Los Angeles, where she was awarded the Woman of the Year prize, wearing a dress from Area featuring a leather strapped corset.
February 2022
Is there a better way to ring in your 19th birthday than with a ‘90s-inspired cowboy ’fit? We don't think so! The star rocked a hot pink silk two-piece by Nφdress with a pair of Mary Jane platform shoes from Naked Wolfe to celebrate her birthday in California. The finishing touch? A pastel pink cowboy hat that fittingly announced the arrival of the “Birthday Girl.” If you want to recreate Liv's look, you can get her skirt here and her oversleeve and camisole set here.
February 2022
London Calling, baby! Rodrigo landed on British soil with perhaps the most weather-appropriate ‘fit of all times. The singer kept warm and cozy with multiple layers and also took pattern and texture clashing to another level with the ’fit. While playing tourist in the English capital, the star donned a crocheted sweater, crocheted hat, a small bag on her shoulder, blue fishnet tights, and, of course, the OR staple: chunky shoes. (She is also wearing theDasha Micro Skirtby Edikted under the layers.) The very definition of eclectic and we are loving every bit of it. (After all, you know what they say: When in Rome London…)
January 2022
Yes, gorgeous, gorgeous girls are outfit repeaters — and, of course, Rodrigo is a gorgeous, gorgeous girl. On January 26, Rodrigo took to Instagram to share a few pics of the outfit she wore to Interscope’s 30th-anniversary exhibition at LACMA and we are spotting a familiar pair of boots. Yes, Rodrigo once again rocked the Marc Jacobs platform boots that once made her go viral, and, honestly, we love to see it. (The rest of her outfit, according to her stylists, is also from Marc Jacobs's Heaven line, which we know Liv loves.)
December 2021
Rodrigo looked peak Olivia Rodrigo at the 2021 Teen Vogue Summit with a pair of Dr. Martens, of course.
December 2021
A big bow for Variety's Hitmakers event because she's a gift. (Her dress was Calvin Luo.)
November 2021
Another day, another YSL 'fit by Rodrigo. The star rocked a quintessential Saint Laurent look (black pointy pumps, black tights, and a tiny black dress) while attending Art Basel in Miami Beach with the brand.
November 2021
During the 2021 AMAs, Rodrigo looked stunning in her sequined and feathered periwinkle gown by David Koma. She paired the figure-hugging dress with some silver pumps that showed off her matching pedicure.
October 2021
Olivia Rodrigo was seen on her way to Jimmy Kimmel Live on October 26, 2021, clad in one of her trademark '90s-inspired grunge ensembles. The star rocked a plaid corset, a green satin midi shirt, Doc Martens, and a Heaven by Marc Jacobs Virgin Suicides bag.
September 2021
On September 25, Rodrigo attended the Academy Museum of Motion Pictures opening gala in Los Angeles wearing this showstopping gown from Saint Laurent. She paired the look with a classic red lip and a simple but effective updo that also perfectly framed her face. While it is true that Rodrigo didn't look the most comfortable in this ensemble — maybe because the fit wasn't 100% perfect — the whole thing was stunningly gorgeous and it is, without a doubt, her most sophisticated look to date.
September 2021
If you ever wondered what Rodrigo's take on Parisian style would look like, wonder no more. While in Las Vegas, Rodrigo channeled her inner French gal (while letting her edgy side shine) with vintage Jean Paul Gaultier jeans, a crocheted beret, and a black corset bustier worn as a top. Her style inspiration for the look? None other than Sex and the City's Carrie Bradshaw. (Swipe until the last slide above to see for yourself).
September 2021
For her MTV VMAs 2021 performance (and to receive her first Moon Person award), Rodrigo rocked this pastel dress from Marc Jacob's Heaven line. The purple and baby sky blue dress was custom-made for the artist. The collaboration makes total sense and works perfectly for Liv. She rounded off the look with a Swarovski choker, Wolford tights, and, of course, a pair of Dr. Martens x Heaven by Marc Jacobs croc boots.
September 2021
On the red carpet, Rodrigo wore this stunning Atelier Versace dress and archive Richard Kerr butterfly earrings.
August 2021
By now, we all know Rodrigo has a penchant for platform boots, but she really took it to the next level with this Bratz-esque pair: the second Marc Jacobs pair in her arsenal (that we know of.)
Rodrigo stepped out in Los Angeles with Iris Apatow wearing a pair of the archive shoes, which were first unveiled during the Marc Jacobs Fall 2017 show. This silhouette, known as the Margaret, and her low-rise sister, the Ruth, have recently seen a spike in popularity as they are being sold once again at the Heaven by Marc Jacobs boutique in Los Angeles' Fairfax area.
July 2021
Rodrigo attended the launch party of Billie Eilish's new album, Happier Than Ever, in a stunning two-piece that she paired, of course, with Dr. Martens and silver jewelry.
July 2021
Rodrigo was spotted out and about in NYC, grabbing lunch and doing a bit of thrifting with Conan Gray in one of her most buzz-worthy outfits to date. The singer rocked a pair of white sunglasses, a graphic t-shirt from Mimi Wade, and a statement mini skirt. However, the stars of the outfit were without doubt her TikTok-approved Mayhem red patent platform boots from Naked Wolfe. (If “Oops!...I Did It Again” were a shoe, it'd be these.)
July 2021
On July 14, Olivia Rodrigo arrived at the White House to promote COVID-19 vaccination among young people and she did so in an impeccable outfit. The star opted for a tweed Chanel two-piece and her trusty silver jewelry. To contrast the baby pink of the ensemble, she added a black mini purse and black socks paired with platform Mary Janes in white. A mix of Clueless's Cher Horowitz and Legally Blonde's Elle Woods, this outfit is more than perfect for the formal occasion.
June 2021
Rodrigo's current style lays at a mix of Gen-Z flare and early '00s grunge. This outfit is a perfect example of that: a DSQUARED2 red plaid print dress paired with Marc Jacobs knee-high platform heels with cutouts all the way up the front. Perfection.
May 2021
Performing her hit single "Good 4 U" for the first time on Saturday Night Live, Rodrigo went peak Gen-Z will her outfit: Plaid jumpsuit, Dr. Martens boots, and all the angst you could ask for. The look was a contrast from Rodrigo's previous outfit for the evening. While performing "Drivers License," she donned a silk slip dress, matching the mood of the chart-topping tune. The juxtaposition between the two outfits showed Olivia Rodrigo's style range clearly, in just one evening.
May 2021
To promo her debut SNL performance, Rodrigo slipped into a shiny burgundy dress, cut at the mid-thigh but complete with sleeves. She paired it with a black face mask and threw her hair into two braids, which has since become one of her go-to 'dos.
May 2021
Rodrigo is not afraid to play with bold patterns and prints. Spotted on the streets of New York City leading up to her SNL debut performance, she sported a funky cat-print dress, worn on top of a black shirt. Rodrigo finished off the look with neon green sunglasses and black Converse low tops.
May 2021
Rodrigo showed up to her SNL rehearsal in this to die for ensemble: Beneath a classic leather jacket, Rodrigo opted for a two-piece neon green and black beaded set from Erika Maish. She completed the look with knee-high, lace-up boots. One word: Fabulous.
May 2021
For her first trip to London, Rodrigo did not disappoint on the fashion front. I mean, Marc Jacobs and Jean Paul Gaultier? Doesn’t get much more iconic! In her Hot Ones interview, Rodrigo admitted she loved this outfit so much she had to wear it twice in a row because she couldn’t secure a picture the first time. And we are glad she did!
May 2021
Performing her hit single "drivers license" in front of Taylor Swift, Harry Styles, and fellow artists in the audience, Rodrigo took the stage of the BRIT Awards in a stunning custom red gown by Dior. The look — created in part by London-based stylist Anna Hughes-Chamberlain — combined a sheer red dress with a matching sequin bra and a short set beneath. It was bold, powerful, yet elegant, matching the song's soulful fire.
May 2021
Prior to performing, Rodrigo walked the red carpet of the BRIT Awards in another Dior ensemble. Opting for another bold color, Olivia Rodrigo donned a strapless neon green tulle gown, paired with jewelry from Alexander Lee McQueen's right-hand man Shaun Leane. She completed the look with a simple, understated black belt and heels. It was classy yet flavorful, just as we've come to expect from Rodrigo.
May 2021
Sour? More like sweet, if you ask me! Rodrigo rocked this extravagant pink gown on Instagram, pairing it with some spiky neck jewelry to counteract its sweet vibe.
April 2021
Pattern clashing can be a big no for most of us, but Rodrigo pulls it off effortlessly. (And you can never go wrong with a pair of Vans slip-ons and matching socks!)
March 2021
This candid pic perfectly encapsulates Olivia Rodrigo's laid-back style. Dr. Martens Jadons, a pair of Y2k printed jeans, a graphic tee, and a leather jacket. Can you tell she's that girl?
February 2021
Dr. Martens Jadons are a staple in Olivia Rodrigo's wardrobe, and she pairs them with everything, including polka-dot dresses.
January 2021
Rodrigo rang in 2021 in this stunning butterfly top with matching eye makeup.
January 2021
Converse, leather, and a layered sweater give Rodrigo's go-to look a preppier and winter-approved twist.
November 2019
Spotted in New York City, Olivia Rodrigo was serving some Cruella de Vil realness with this look: White furry coat with a red top, blue jeans, and matching red heels. Before her "drivers license" fame, there was no doubt Rodrigo was destined for greatness.
November 2019
At the Disney+ premiere of High School Musical: The Musical: The Series, Olivia Rodrigowalked one of her first major red carpets, in style, of course. Stealing the spotlight with her over-the-top ensemble, Rodrigo went for a simple white t-shirt, paired with an eye-catching black tulle gown, finished with flower embellishes for a little pop of glamour.
October 2019
For an event in Hollywood, Rodrigo went the simple yet chic route, slipping into a pair of high-waisted trousers with a white t-shirt and a light-wash denim jacket. The look is mature but still matches her teenage glow.
September 2019
At the World Premiere of Disney's Maleficent: Mistress of Evil, Rodrigo looked, well, magical. This shimmery gold ensemble is fun and festive for the occasion, combining classic Disney energy with red carpet status.
August 2019
Rodrigo achieved peak cuteness at the D23 Disney Legends event, wearing a simple white turtleneck with burgundy suede pants. During this time, Olivia Rodrigo's style was simple yet perfectly curated. Still a young teenager, she never looked out of place. Rather, she was always put together, representing the classy woman she knew she'd become.
October 2018
While Rodrigo doesn't wear all-black 'fits too often anymore, she certainly did back in her early style days. This dress is fun, youthful and, while dark in color, it still finds a way to let her natural glow shine through.
June 2018
This pic is from a while ago, but Rodrigo looks just as mature as she does today. Attending the World Premiere of Disney and Pixar's Incredibles 2, Rodrigo wore a pair of high-waisted, green stain paints with a black and white polka-dot top. She paired the ensemble with some black heels and kept everything else simple. Rodrigo has never been one to overdue her looks, especially on the red carpet, and that's exactly why they work so well.
April 2018
In this printed black and red mini dress, Rodrigo looks like a Valentine's Day dream come true, even if she sported this particular ensemble in April. Rodrigo paired the dress with some darker eye makeup, heavier on the eyeliner and mascara than we've become accustomed to these days.
December 2017
Pretty in pink, this is one of the few pictures we have of the star with her hair up in a messy bun.
November 2017
Wearing all red, Rodrigo's baby face was on full display at the premiere of Coco. Matching this simple red dress with perfectly matching heels, Rodrigo showed how clean yet sophisticated her style was becoming.
October 2017
Another one of Rodrigo's rare, early all-black moments at the World Premiere of Marvel Studios' Thor: Ragnarok.
May 2017
This is years ago but Rodrigo looks just as put together as she does today. Simple and adorable, this dress matches her joyful persona perfectly. (And that hair!)
May 2017
Like many fellow Disney Channel stars, Rodrigo used her early teenage years to experiment with style, especially in 2017. At the premiere of Warner Bros. Pictures' Everything, Everything, she matched two very different prints together: a polka-dot top and a layered, striped skirt. As opposed to her current style, the look was a lot. But we love to see how far Rodrigo has grown, and which style choices led her to where she is today!
December 2016
Another bold choice: This mix-matched ensemble for the PAWS FURR CAUSES Benefit for Lifelineforpets. And while that top may now be a bit outdated, there's no denying that Rodrigo could still rock that skirt today, and it would fit perfectly in with her current grunge-inspired closet.
October 2016
Throw on a leather jacket and some knee-high platform boots, and this is definitely a look Rodrigo could still pull off today.
August 2016
Baby Olivia Rodrigo! With her hair slicked back and makeup done bright and pretty, her youthful glow is shining through in this ensemble.
July 2016
While Rodrigo would likely never be caught dead wearing ripped jeans on the red carpet today, there was a time when she did. It's all a part of the evolutionary style journey!
July 2016
From jeans to sophisticated in a flash, Rodrigo was showing her already developed diversity of style even in 2016.
June 2016
This exaggerated sleeve moment? Ok, baby Rodrigo!
June 2016
At the premiere of Finding Dory, Rodrigo paired this beautiful floral skirt with a simple black top. It's moments like these that show us how far her style has come, but also how authentic it has remained.
November 2015
That hair! Those shoes! The mix-matched denim! Baby Olivia Rodrigo was truly the cutest. Little did she know the journey that would lie ahead.
Originally Appeared on Teen Vogue
