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Olivia Rodrigo Refines On-stage Boot Aesthetic for Surprise Disney Upfront Performance

She wore a black block heel boot for the occasion.

Olivia Rodrigo performed a surprise set to close out the Disney Upfront in New York City on Tuesday, and she brought her signature style with her.

CORPORATE - 5/12/26 - The Disney Advertising Upfront is a showcase event that brings together all the content corners of The Walt Disney Company on one stage.  On Tuesday, May 12, 2026 at North Javits in New York City, an incredible roster of all-star talent will tout their connections to storytelling, Disney, and each other while showcasing their latest projects for the upcoming year.
(Disney/Jennifer Pottheiser)  
OLIVIA RODRIGO  (Photo by Jennifer Pottheiser/Disney via Getty Images)
Olivia Rodrigo Jennifer Pottheiser/Disney via Getty Images

Rodrigo, who is promoting her upcoming third studio album “you seem pretty sad for a girl so in love,” performed three songs from her discography: “get him back,” “good 4 u” and her new single “drop dead” off the awaited album.

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A closer look at Olivia Rodrigo's boots.
A closer look at Olivia Rodrigo’s boots. Michael Le Brecht II/Disney via Getty Images

Rodrigo loves a statement boot to complete her on-stage looks, and this occasion was no different. As opposed to an edgy lace-up Dr. Martens style, she went with a simple silhouette featuring a calf-height shaft, modest block heel and narrow toe.

CORPORATE - 5/12/26 - The Disney Advertising Upfront is a showcase event that brings together all the content corners of The Walt Disney Company on one stage.  On Tuesday, May 12, 2026 at North Javits in New York City, an incredible roster of all-star talent will tout their connections to storytelling, Disney, and each other while showcasing their latest projects for the upcoming year.
(Disney/Michael Le Brecht II)  
OLIVIA RODRIGO  (Photo by Michael Le Brecht II/Disney via Getty Images)
Olivia Rodrigo Michael Le Brecht II/Disney via Getty Images

The zip-up boot was made more complex with its shiny crinkled-effect material, bringing a bit of bite to her ensemble. The rest of her look included a pale pink merino wool cardigan from Courrèges with a buckle detail at the collar, and a dark pleated mini skort from Sandy Liang.

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CORPORATE - 5/12/26 - The Disney Advertising Upfront is a showcase event that brings together all the content corners of The Walt Disney Company on one stage.  On Tuesday, May 12, 2026 at North Javits in New York City, an incredible roster of all-star talent will tout their connections to storytelling, Disney, and each other while showcasing their latest projects for the upcoming year.
(Disney/Michael Le Brecht II)  
OLIVIA RODRIGO  (Photo by Michael Le Brecht II/Disney via Getty Images)
Olivia Rodrigo Michael Le Brecht II/Disney via Getty Images

Rodrigo’s latest on-stage footwear moment is a more toned-down design in her concert boot lineup. She often reaches for lace-up Dr. Martens boots, with the platform Audrick 20-Eye Knee High Boots being a go-to selection for the 23-year-old musician.

She recently softened up her shoe aesthetic for her double duty appearance on “Saturday Night Live,” wearing Aquazzura’s crystal-embellished pink Tell Me sandals and Miu Miu’s pink satin ballet flats, the latter of which she paired with knit legwarmers. Rodrigo also wore Miu Miu ballet flats back in October, a green pair layered with white knee-high socks, to accompany a crystal-embellished dress from the Prada subsidiary.