Olivia Rodrigo: See Her Complete Style Evolution

  • Oops!
    Something went wrong.
    Please try again later.
·15 min read
In this article:
  • Oops!
    Something went wrong.
    Please try again later.

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.

All products featured on Teen Vogue are independently selected by our editors. However, when you buy something through our retail links, we may earn an affiliate commission.

September 2021

<h1 class="title">Academy Museum of Motion Pictures Opening Gala - Red Carpet</h1><cite class="credit">Stefanie Keenan/Getty Images for Academy Museum of Motion Pictures </cite>

Academy Museum of Motion Pictures Opening Gala - Red Carpet

Stefanie Keenan/Getty Images for Academy Museum of Motion Pictures

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

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

<h1 class="title">The 2021 Met Gala Celebrating In America: A Lexicon Of Fashion - Arrivals</h1><cite class="credit">Theo Wargo/Getty Images</cite>

The 2021 Met Gala Celebrating In America: A Lexicon Of Fashion - Arrivals

Theo Wargo/Getty Images

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

<h1 class="title">2021 MTV Video Music Awards - Show</h1><cite class="credit"> Kevin Mazur/MTV VMAs 2021/Getty Images for MTV/ViacomCBS</cite>

2021 MTV Video Music Awards - Show

Kevin Mazur/MTV VMAs 2021/Getty Images for MTV/ViacomCBS

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

<h1 class="title">2021 MTV VMAs</h1><cite class="credit">Udo Salters /Patrick McMullan via Getty Images</cite>

2021 MTV VMAs

Udo Salters /Patrick McMullan via Getty Images

On the red carpet, Olivia wore this stunning Atelier Versace dress and archive Richard Kerr butterfly earrings.

August 2021

<h1 class="title">Celebrity Sightings In Los Angeles - August 15, 2021</h1><cite class="credit">Bellocqimages/Bauer-Griffin/GC Images</cite>

Celebrity Sightings In Los Angeles - August 15, 2021

Bellocqimages/Bauer-Griffin/GC Images

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

<h1 class="title">Billie Eilish And Spotify Celebrate "Happier Than Ever: The Destination" For Her New Album</h1><cite class="credit">Matt Winkelmeyer</cite>

Billie Eilish And Spotify Celebrate "Happier Than Ever: The Destination" For Her New Album

Matt Winkelmeyer

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

<h1 class="title">EXCLUSIVE: Olivia Rodrigo Looks Stylish In NYC As She Steps Out For Lunch With Fellow Hitmaker Conan Gray In Shiny Red Platform Boots.</h1><cite class="credit">Christopher Peterson / SplashNews.com</cite>

EXCLUSIVE: Olivia Rodrigo Looks Stylish In NYC As She Steps Out For Lunch With Fellow Hitmaker Conan Gray In Shiny Red Platform Boots.

Christopher Peterson / SplashNews.com

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

<h1 class="title">Pop Star Olivia Rodrigo Arrives At The White House To Record Videos Promoting Covid Vaccinations</h1><cite class="credit">Chip Somodevilla/Getty Images </cite>

Pop Star Olivia Rodrigo Arrives At The White House To Record Videos Promoting Covid Vaccinations

Chip Somodevilla/Getty Images

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

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

Who else could rock a Twilight purse with this killer (and summery) all-black 'fit?

June 2021

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

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

<h1 class="title">Saturday Night Live - Season 46</h1><cite class="credit">Will Heath/NBC/NBCU Photo Bank via Getty Images</cite>

Saturday Night Live - Season 46

Will Heath/NBC/NBCU Photo Bank via Getty Images

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

<h1 class="title">Saturday Night Live - Season 46</h1><cite class="credit">Rosalind O'Connor/NBC/NBCU Photo Bank via Getty Images</cite>

Saturday Night Live - Season 46

Rosalind O'Connor/NBC/NBCU Photo Bank via Getty Images

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

<h1 class="title">Celebrity Sightings In New York City - May 14, 2021</h1><cite class="credit">Robert Kamau/GC Images via Getty</cite>

Celebrity Sightings In New York City - May 14, 2021

Robert Kamau/GC Images via Getty

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

<h1 class="title">Celebrity Sightings In New York City - May 13, 2021</h1><cite class="credit">Robert Kamau/GC Images via Getty</cite>

Celebrity Sightings In New York City - May 13, 2021

Robert Kamau/GC Images via Getty

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

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

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

<h1 class="title">The Brit Awards 2021 - Show - London</h1><cite class="credit">Ian West/PA Images via Getty Images</cite>

The Brit Awards 2021 - Show - London

Ian West/PA Images via Getty Images

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

<h1 class="title">The BRIT Awards 2021 - Media Room</h1><cite class="credit">JMEnternational/JMEnternational for BRIT Awards/Getty Images</cite>

The BRIT Awards 2021 - Media Room

JMEnternational/JMEnternational for BRIT Awards/Getty Images

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

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

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

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

Marine Serre and band tees for a photobooth photo sesh? We approve.

April 2021

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

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

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

Olivia welcomed summer earlier with this bikini pic, and maaany Pinterest boards appreciated the heads-up.

March 2021

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

A Powerpuff Girls-inspired Wildflower phone case that matches your corset-style top? 10/10.

March 2021

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

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

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

Dr. Martens Jadons are a staple in Olivia's wardrobe and she pairs them with everything, including polka-dot dresses.

January 2021

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

Olivia rang in 2021 in this stunning butterfly top with matching eye makeup.

January 2021

<cite class="credit">Courtesy of Olivia Rodrigo/Instagram @<a href="https://www.instagram.com/oliviarodrigo/" rel="nofollow noopener" target="_blank" data-ylk="slk:oliviarodrigo" class="link rapid-noclick-resp">oliviarodrigo</a></cite>
Courtesy of Olivia Rodrigo/Instagram @oliviarodrigo

Converse, leather, and a layered sweater give Olivia's go-to look a preppier and winter-approved twist.

November 2019

<h1 class="title">Celebrity Sightings In New York City - November 05, 2019</h1><cite class="credit">Raymond Hall/GC Images via Getty</cite>

Celebrity Sightings In New York City - November 05, 2019

Raymond Hall/GC Images via Getty

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

<h1 class="title">Premiere Of Disney+'s "High School Musical: The Musical: The Series" - Red Carpet</h1><cite class="credit">Kevin Winter/Getty Images</cite>

Premiere Of Disney+'s "High School Musical: The Musical: The Series" - Red Carpet

Kevin Winter/Getty Images

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

<h1 class="title">Ad Council's Creators For Good Host She Can STEM (Science, Technology, Engineering & Math) Summit</h1><cite class="credit">Paul Archuleta/Getty Images</cite>

Ad Council's Creators For Good Host She Can STEM (Science, Technology, Engineering & Math) Summit

Paul Archuleta/Getty Images

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

<h1 class="title">World Premiere Of Disney's “Maleficent: Mistress Of Evil" - Arrivals</h1><cite class="credit">Axelle/Bauer-Griffin/FilmMagic via Getty</cite>

World Premiere Of Disney's “Maleficent: Mistress Of Evil" - Arrivals

Axelle/Bauer-Griffin/FilmMagic via Getty

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

<h1 class="title">D23 Expo 2019</h1><cite class="credit">Frazer Harrison/Getty Images</cite>

D23 Expo 2019

Frazer Harrison/Getty Images

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

<h1 class="title">2018 Chinese American Film Festival Opening Ceremony And Golden Angel Awards Ceremony</h1><cite class="credit">Rodin Eckenroth/Getty Images</cite>

2018 Chinese American Film Festival Opening Ceremony And Golden Angel Awards Ceremony

Rodin Eckenroth/Getty Images

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

<h1 class="title">Premiere Of Disney And Pixar's "Incredibles 2" - Arrivals</h1><cite class="credit">Jean Baptiste Lacroix/WireImage via Getty</cite>

Premiere Of Disney And Pixar's "Incredibles 2" - Arrivals

Jean Baptiste Lacroix/WireImage via Getty

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

<h1 class="title">My Friend's Place 30th Anniversary Red Carpet and Gala</h1><cite class="credit">Vivien Killilea/Getty Images for My Friend's Place</cite>

My Friend's Place 30th Anniversary Red Carpet and Gala

Vivien Killilea/Getty Images for My Friend's Place

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

<h1 class="title">The Actors Fund's 2017 Looking Ahead Awards Honoring The Youth Cast Of NBC's "This Is Us" - Arrivals</h1><cite class="credit">Leon Bennett/Getty Images </cite>

The Actors Fund's 2017 Looking Ahead Awards Honoring The Youth Cast Of NBC's "This Is Us" - Arrivals

Leon Bennett/Getty Images

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

<h1 class="title">Premiere Of Disney Pixar's "Coco" - Arrivals</h1><cite class="credit">Jason LaVeris/FilmMagic via Getty</cite>

Premiere Of Disney Pixar's "Coco" - Arrivals

Jason LaVeris/FilmMagic via Getty

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

<h1 class="title">The World Premiere Of Marvel Studios' "Thor: Ragnarok"</h1><cite class="credit">Rich Polk/Getty Images for Disney</cite>

The World Premiere Of Marvel Studios' "Thor: Ragnarok"

Rich Polk/Getty Images for Disney

Another one of Olivia's rare all-black moments at the World Premiere of Marvel Studios' Thor: Ragnarok.

May 2017

<h1 class="title">Premiere Of Disney's "Pirates Of The Caribbean: Dead Men Tell No Tales" - Arrivals</h1><cite class="credit">Jon Kopaloff/FilmMagic via Getty</cite>

Premiere Of Disney's "Pirates Of The Caribbean: Dead Men Tell No Tales" - Arrivals

Jon Kopaloff/FilmMagic via Getty

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

<h1 class="title">Screening Of Warner Bros. Pictures' "Everything, Everything" - Arrivals</h1><cite class="credit">David Livingston/Getty Images</cite>

Screening Of Warner Bros. Pictures' "Everything, Everything" - Arrivals

David Livingston/Getty Images

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

<h1 class="title">Paws Furr Causes Benefit For Lifelineforpets</h1><cite class="credit">Tasia Wells/Getty Images</cite>

Paws Furr Causes Benefit For Lifelineforpets

Tasia Wells/Getty Images

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

<h1 class="title">Premiere Of Disney Channel's "The Swap" - Arrivals</h1><cite class="credit">Tommaso Boddi/WireImage via Getty</cite>

Premiere Of Disney Channel's "The Swap" - Arrivals

Tommaso Boddi/WireImage via Getty

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

<h1 class="title">Destination: Disney Style Launch Event</h1><cite class="credit">Lester Cohen/Getty Images for Disney Consumer Products</cite>

Destination: Disney Style Launch Event

Lester Cohen/Getty Images for Disney Consumer Products

Baby Olivia! With her hair slicked back and makeup done bright and pretty, her youthful glow is shining through in this ensemble.

July 2016

<h1 class="title">Baby Kaely's End Of Summer Bash</h1><cite class="credit">David Livingston/Getty Images</cite>

Baby Kaely's End Of Summer Bash

David Livingston/Getty Images

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

<h1 class="title">4th Annual Beautycon Festival Los Angeles - Arrivals</h1><cite class="credit">Amanda Edwards/WireImage via Getty</cite>

4th Annual Beautycon Festival Los Angeles - Arrivals

Amanda Edwards/WireImage via Getty

From jeans to sophisticated in a flash, Olivia was showing her already developed diversity of style even in 2016.

June 2016

<h1 class="title">Premiere Of 100th Disney Channel Original Movie "Adventures In Babysitting" And Celebration Of All DCOMS - Arrivals</h1><cite class="credit">Michael Tullberg/Getty Images</cite>

Premiere Of 100th Disney Channel Original Movie "Adventures In Babysitting" And Celebration Of All DCOMS - Arrivals

Michael Tullberg/Getty Images

This exaggerated sleeve moment? Ok, baby Olivia!

June 2016

<h1 class="title">The World Premiere Of Disney-Pixar's "Finding Dory" - Arrivals</h1><cite class="credit">Jason LaVeris/FilmMagic via Getty</cite>

The World Premiere Of Disney-Pixar's "Finding Dory" - Arrivals

Jason LaVeris/FilmMagic via Getty

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

<h1 class="title">P.S. ARTS Presents Express Yourself 2015 - Arrivals</h1><cite class="credit">Michael Tran/FilmMagic via Getty</cite>

P.S. ARTS Presents Express Yourself 2015 - Arrivals

Michael Tran/FilmMagic via Getty

That hair! Those shoes! The mix-matched denim! Baby Olivia was truly the cutest. Little did she know the journey that would lie ahead.

Let us slide into your DMs. Sign up for the Teen Vogue daily email.

Want more from Teen Vogue? Check this out:

Originally Appeared on Teen Vogue