Olivia Rodrigo’s aesthetic is as much a tribute to the past as it is a blueprint for modern pop style.
Frequently drawing from the grunge and “cool-girl” silhouettes of the late 1990s and early 2000s, the Grammy-winning artist has become a central figure in the Y2K style revival.
💫 Jump to a Look:
A definitive example of this vintage-inspired approach was on display at the 65th Annual Grammy Awards in Los Angeles, when she leaned into a minimalist “naked dress” aesthetic that felt both nostalgic and era-appropriate.
Olivia Rodrigo Brings ’90s Minimalism to the Grammys in Custom Miu Miu
Nicknamed the Y2K revival style icon, Rodrigo arrived in a minimalist ‘90s slip dress custom-designed by Miu Miu.
She went commando in the black number made of sheer fabric, a trend that dominated the 1990s. Her dress featured a cleavage-baring neckline, spaghetti straps, and a form-fitting floor-length silhouette.
Olivia Rodrigo steps onto the 65th Annual Grammy Awards red carpet in Los Angeles on February 5, 2023, wearing a sheer black Miu Miu slip dress layered over lingerie and finished with minimalist open-toe black heels that elongate the silhouette with understated precision (Credit: BauerGriffin / INSTARimages)
The Drivers License hitmaker layered the provocative “naked” dress over a black bra and matching underwear for some coverage. She slipped her black pedicured feet into a pair of black open-toe heels for a streamlined finish.
With the help of stylist Danielle Goldberg, whose clients also include Laura Harrier and Kaia Gerber, Rodrigo kept the look minimalist, pairing it with Tiffany & Co. jewelry.
She wore rings and stud earrings, accentuating her décolletage with the “Big Bean” black lacquer silk cord pendant necklace.
Olivia Rodrigo commands attention in a ’90s see-through sheer black dress with black lingerie underneath (Credit: BauerGriffin / INSTARimages)
Rodrigo was not up for any awards, but she took to the stage to present the Best New Artist award, which went to jazz singer Samara Joy McLendon.
For her beauty glam, the Filipino American star opted for a natural look, with makeup artist Nina Park using YSL Beauty to enhance her features. She wore winged eyeliner, mascara, a hint of peachy blush and matching eyeshadow, and a swipe of subtle red lip gloss.
Olivia then wore her shiny tresses in a sleek blowout, done by hairstylist Bryce Scarlett.
Olivia Rodrigo opts for minimal makeup, with mascara and winged eyeliner, and styles her hair straight, cascading down her back (Credit: BauerGriffin / INSTARimages)
Olivia Rodrigo Switches Into a Y2K Party Look in 16Arlington Sequins
Later that evening, Olivia Rodrigo slipped out of her see-through dress and into a sparkling mini while attending Universal Music Group’s Grammy Awards after-party.
Wearing another Y2K look, the singer opted for a black dress decked out in sequins by 16Arlington, a London-based brand founded in 2017 by Marco Capaldo and the late Federica “Kikka” Cavenati.
Olivia Rodrigo joins Universal Music Group’s Grammy Awards after-party in a black 16Arlington sequined mini dress with a front keyhole and an open back design (Credit: Xavier Collin / Image Press Agency / ABACA / INSTARimages / Cover Images)
The $1,393 custom Solaria dress featured long bell sleeves, a front-tie closure creating a large keyhole cutout at the chest, an open back, and a thigh-skimming hem.
Olivia went bare-necked and simply accessorized with silver stud earrings, letting the shimmering number do the talking.
Olivia Rodrigo turns to reveal the open-back detail of her black 16Arlington sequined mini dress at Universal Music Group’s Grammy Awards after-party, with delicate strap fastenings and shimmering embellishments amplifying the look’s sultry, Y2K-inspired edge (Credit: Xavier Collin / Image Press Agency / ABACA / INSTARimages / Cover Images)
Looking party-ready, Olivia parted her tresses in the middle and styled them in loose curls. She then wore the same beauty look, with cat eyeliner and mascara.
Olivia Rodrigo completes her retro after-party look with black nail polish and Paris Texas’ Tatiana platform sandals (Credit: Xavier Collin / Image Press Agency / ABACA / INSTARimages / Cover Images)
Olivia Rodrigo Finishes the Look With Paris Texas “Tatiana” Platform Sandals
She completed her ensemble with the Paris Texas “Tatiana” sandals. They are made from glossy patent black leather with a slender ankle strap, a square toe, a thick platform, and a 5-inch block heel.
The Paris Texas Tatiana sandals boast a trendy square toe and a slender ankle strap set atop a 5-inch block heel
From ’90s Minimalism to Y2K Sparkle: Why Olivia Rodrigo’s Shoe Choices Always Complete the Story
Whether she’s leaning into sheer, slip-dress minimalism or stepping out in high-shine party sequins, Olivia Rodrigo consistently uses footwear to anchor the mood of each look.
From understated black heels that sharpen a barely-there silhouette to bold platforms that amplify her Y2K influences, her shoe choices are never an afterthought—they’re the final, defining detail. Explore more of her standout style moments below.
👠 Explore Olivia Rodrigo’s Best Shoe & Fashion Moments:
- 📏 Standing at 5’4″ (162.6 cm) and wearing a US shoe size 7, Olivia Rodrigo brings a cool, clean kind of drama to the red carpet, often using sharp silhouettes and statement heels to give her vintage-leaning style extra impact.
- ✨ The Swarovski-soaked VMAs moment with Roger Vivier platforms showed her in full high-glam mode, balancing a crystal-heavy Ludovic de Saint Sernin gown with metallic silver sandals that added sculptural height without overpowering the dress.
- 🔥 Her cut-out Saint Laurent gown and Amber sandals delivered a darker, more directional side of Rodrigo’s style, proving how a sharply cut black dress and sleek ankle-strap heels can feel both youthful and polished.
- 🤍 Olivia’s white Gucci dress with silver Bamboo heels leaned into quiet elegance, with the slim metallic sandals bringing just enough shine and architectural interest to elevate the clean column silhouette.
- 🎀 Her crystal socks and Nodaleto Mary Jane pumps remain one of her most playful fashion turns, channeling a witty, retro-schoolgirl mood while showing how she makes trend pieces feel personal rather than costume-like.