Olivia Rodrigo: From Y2K Dream to Red-Carpet Queen

September 17, 2025

Over the last few years, Olivia Rodrigo has evolved from an up-and-coming pop star to a Gen-Z style and fashion icon for her daring style, whether it is vintage glamour or a mini-dress. Whether it is walking on the red carpet or emulating grungy stage looks, her dress moment has taken fans and fashion watchers by storm. Let's take a glance at some of her most memorable
dress outfits that showcase her evolving sense of style.

1. Little Black Dress with a Cutout – UMG After-Party (2023 Grammys)

At the Grammy after-party hosted by Universal Music Group, Olivia wore a latest little black dress with a front cutout. She finished off the look with a pair of her signature platform heels for an effortlessly sassy
vibe.

2. Thom Browne Gown – 2023 Met Gala

Rodrigo wore a black and white Thom Browne gown inspired by Karl Lagerfeld for the Met Gala in 2023. The flower touches to the structured silhouette of her outfit indicate her ability to perfect a combination of different looks.

3. Vintage 1994 Chanel Cocktail Dress – Met Gala After-Party

Following the main gala, she slipped into a vintage Chanel 1994 cocktail dress. Her choice showed her love for vintage pieces and entrenching her status as a style influencer.

4. White Minidress by Patou – BBC Radio 1, London (Aug 2023)

Olivia gave a head turner moment in a colorful white Patou minidress worn with matching LOQ boots. The all-white outfit had a clean and modern polish that looked young.

5. Versace Purple Gown – 2022 Met Gala

At her second Met Gala, she stunned in a purple Versace gown with high slit and Old Hollywood vibes. De Beers jewelry matched with butterfly hair accessories complete the look and took us back to her “Sour” era.

6. Area Maxi Dress – Billboard Women in Music (2022)

A flowing Area maxi dress was worn by Olivia when she took home the Woman of the Year award. The
delicate dress paired with the chunky black boots created an interesting contrast between delicate and rugged.

7. Saint Laurent Column Dress – Academy Museum Opening Gala

Rodrigo wore a strapless Saint Laurent column gown with a plunging neckline and a high slit at the Academy Museum of Motion Pictures inaugural gala. This look was a major step forward in her red carpet evolution,
as it marries sophistication with modern sultriness.

8. Lace Saint Laurent Catsuit – 2021 Met Gala

For the first time at the Met Gala, Olivia wowed everyone with a sheer black lace catsuit by Saint Laurent. In a style that was film star beautiful and a little punk rock, Vanessa Kirby’s fluid, body-kissing dress was off-the-shoulder and skin-tight. It was a dress that made it clear she was ready to claim a spot in fashion’s A-list.

9. David Koma Sequined Purple Dress – 2021 AMAs

At the American Music Awards, she wore a sparkling purple mini-dress from David Koma, exuding a youthful glow. Further, she is known for her fun and playful way of dressing.

10. Heaven by Marc Jacobs Lilac Dress – MTV VMAs (Performance Look)

At the MTV VMAs, Olivia performed Good 4 U while wearing a custom lilac dress by Heaven by Marc Jacobs. She completed the look with matching gloves, butterfly hair clips, fishnet tights, and Doc Martens with a rebellious meets romantic vibe that became iconic.

11. Pink Mini and Platform Boots – VMA After-Party

To celebrate after the party, she slipped into a pink myriad mini-dress paired with pink heels, or also in some pictures, matching purple platform boots. The combination was youthful and fun, filled with pops of color that jumped off the red carpet.

12. Slip Dress with Green Bow – Variety Hitmakers Brunch

At Variety’s Hitmakers Brunch, Olivia looked chic and simple in Calvin Luo. The actress wore a slip black dress with a large green bow. She paired it with strappy heels and stockings which shows how less can be more when styled correctly.

How to describe the outfit aesthetic of Olivia Rodrigo?

·
Olivia loves using vintage pieces from the 2000s, like Chanel and butterfly details, in her outfits giving them a twist.

· Tough and sweet: She inventively combines delicate dresses with tough pieces, a maxi and chunky boots, lace and sexy silhouette.

· Her style growth is on the red carpet, with her style getting bolder and more refined with time, from a punkish lace catsuit to a sumptuous gown.

· She also imparts a personal touch to her looks by wearing platform shoes, butterfly clips and bows.

Olivia Rodrigo's dress evolution isn't merely the subject of her outfits. With each public appearance, she proves herself to be bold and authentic. Whether it’s a tiny frock or high-end couture, her outfits are always youthful and red-carpet ready.