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In just a few short months, Olivia Rodrigo has gone from Disney darling to international pop sensation. Her debut album, Sour, has put her on the map as a rising trailblazer, following in the footsteps of legends like Taylor Swift. And with her powerful, beautifully painful voice also comes Olivia's 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 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.
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. 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.
November 2022
Backstage, however, she traded the ensemble for a much comfier option.
October 2022
Olivia attended the Givenchy in Paris wearing an all-white 'fit that combine lace and satin.
September 2022
Olivia 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, Olivia 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 Olivia 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 Olivia herself!)
Though the corset was undoubtedly the star of the (fashion) show, Olivia 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
Olivia 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.
April 2022
For a while, we have seen celebs the likes of Megan Fox and Kylie Jenner wearing bras as a top and now Olivia is hopping on the trend — kind of. In a recent photo dump posted to her Instagram, Olivia 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, Olivia 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.
February 2022
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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
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A pop punk-inspired 'fit and a Chanel flap bag to visit Disneyland? Yes.
February 2022
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London Calling, baby! Olivia 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 the Dasha Micro Skirt by 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, Olivia is a gorgeous gorgeous girl. On January 26, Olivia 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, Olivia 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
Olivia looked peak Olivia 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.
November 2021
Another day, another YSL 'fit by Olivia. The star rocked a quintessential Saint Laurent look (black pointy pumps, black tights, and tiny black dress) while attending Art Basel in Miami Beach with the brand.
November 2021
During the 2021 AMAs, Olivia 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, Olivia 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 Olivia 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
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If you ever wondered what Olivia's take on Parisian style would look like, wonder no more. While in Las Vegas, Olivia 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
On September 13, Olivia Rodrigo made her very chic Met Gala debut wearing a quintessential Saint Laurent ensemble, as she was outfitted by the French maison.
September 2021
For her MTV VMAs 2021 performance (and to receive her first Moon Person award), Olivia 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, Olivia wore this stunning Atelier Versace dress and archive Richard Kerr butterfly earrings.
August 2021
By now, we all know Olivia 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.)
Olivia 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
Olivia 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
Olivia 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
Who else could rock a Twilight purse with this killer (and summery) all-black 'fit?
June 2021
Olivia'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, Olivia 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 Olivia'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's style range clearly, in just one evening.
May 2021
To promo her debut SNL performance, Olivia 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
Olivia 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. Olivia finished off the look with neon green sunglasses and black Converse low tops.
May 2021
Olivia showed up to her SNL rehearsal in this to die for ensemble: Beneath a classic leather jacket, Olivia 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, Olivia 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, Olivia 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, Olivia 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, Olivia walked the red carpet of the BRIT Awards in another Dior ensemble. Opting for another bold color, Olivia 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 Olivia.
May 2021
Sour? More like sweet, if you ask me! Olivia rocked this extravagant pink gown on Instagram, pairing it with some spiky neck jewelry to counteract its sweet vibe.
April 2021
Marine Serre and band tees for a photobooth photo sesh? We approve.
April 2021
Pattern clashing can be a big no for most of us but Olivia pulls it off effortlessly. (And you can never go wrong with a pair of Vans slip-ons and matching socks!)
April 2021
Olivia welcomed summer earlier with this bikini pic, and maaany Pinterest boards appreciated the heads-up.
March 2021
A Powerpuff Girls-inspired Wildflower phone case that matches your corset-style top? 10/10.
March 2021
This candid pic perfectly encapsulates Olivia'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's wardrobe and she pairs them with everything, including polka-dot dresses.
January 2021
Olivia rang in 2021 in this stunning butterfly top with matching eye makeup.
January 2021
Converse, leather, and a layered sweater give Olivia's go-to look a preppier and winter-approved twist.
November 2019
Spotted in New York City, Olivia is 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 Olivia was destined for greatness.
November 2019
At the Disney+ premiere of High School Musical: The Musical: The Series, Olivia walked one of her first major red carpets, in style, of course. Stealing the spotlight with her over-the-top ensemble, Olivia 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, Olivia 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, Olivia looked, well, magical. This shimmery gold ensemble is fun and festive for the occasion, combining classic Disney energy with red carpet status.
August 2019
Olivia achieved peak cuteness at the D23 Disney Legends event, wearing a simple white turtleneck with burgundy suede pants. During this time, Olivia'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 Olivia 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 Olivia's natural glow shine through.
June 2018
This pic is from a while ago, but Olivia looks just as mature as she does today. Attending the World Premiere of Disney and Pixar's Incredibles 2, Olivia 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. Olivia 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, Olivia looks like a Valentine's Day dream come true, even if she sported this particular ensemble in April. Olivia 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, Olivia's baby face was on full display at the premiere of Coco. Matching this simple red dress with perfectly matching heels, Olivia showed how clean yet sophisticated her style was becoming.
October 2017
Another one of Olivia's rare all-black moments at the World Premiere of Marvel Studios' Thor: Ragnarok.
May 2017
This is years ago but Olivia 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, Olivia 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 Olivia 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 Olivia 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 Olivia could still pull off today.
August 2016
Baby Olivia! With her hair slicked back and makeup done bright and pretty, her youthful glow is shining through in this ensemble.
July 2016
While Olivia 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, Olivia was showing her already developed diversity of style even in 2016.
June 2016
This exaggerated sleeve moment? Ok, baby Olivia!
June 2016
At the premiere of Finding Dory, Olivia 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 was truly the cutest. Little did she know the journey that would lie ahead.
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