Watch Sabrina Carpenter and Kacey Musgraves Unite for a Nancy Sinatra Classic Performance

San Francisco’s Outside Lands Festival attendees were in for a treat this past weekend as Sabrina Carpenter and Kacey Musgraves joined forces for a surprise performance of a 1966 Nancy Sinatra classic. Carpenter invited Musgraves onstage as she closed out the night on the Lands End stage the night of August 10.

Carpenter and Musgraves’ iconic collaboration on Sinatra’s “These Boots Are Made For Walkin’” seems to push Carpenter further into the realm of half-Western, half-country pop that she entered into with the release of her 2024 track “Please Please Please.”

Sabrina Carpenter and Kacey Musgraves Join Forces

Tambourine in hand, clad in a sparkly black dress and knee-high platform boots, Sabrina Carpenter addressed the crowd: “I think you know this one Outside Lands, yeah?” As Carpenter rattled her tambourine and the band started the song’s distinct introduction, Kacey Musgraves walked out onstage to a roaring crowd.

Standing side by side on opposite platforms, Musgraves kicks off the song’s first verse as Carpenter dances nearby. The two women come together in unison for the song’s chorus. These boots are made for walking, and that’s just what they’ll do. Their effortless harmonies at the end of their phrases add another layer to the performance, showcasing both women’s musicianship and vocal agility.

The pop stars closed out the song downstage, dancing, bantering, and harmonizing with one another. Their version of the Nancy Sinatra classic was a perfect tribute to the pop star that came decades before them, and the San Francisco crowd unsurprisingly loved it.

This Isn’t The Pop Star’s First Country-Tinged Rodeo

Nancy Sinatra’s half-folk rock, half-country classic is the perfect song for an artist like Kacey Musgraves, who broke out as an alternative country artist in the early aughts. But one couldn’t necessarily fault a listener for thinking Sabrina Carpenter’s connection to the country-tinged track was less obvious—particularly before she released “Please Please Please.”

While Carpenter’s pseudo-disco, cheeky hit “Espresso” took the cultural zeitgeist by storm in the summer of 2024, “Please Please Please” was the singer’s actual first No. 1 single. The chart-topping single has a far more country flavor than her past singles, featuring acoustic guitar, soaring vocals, and Carpenter’s love of tongue-in-cheek lyrics. (Case in point: her pleading chorus ending with a gravelly, I beg you don’t embarrass me, motherf*****.)

Carpenter’s inclusion of a country-adjacent track like Nancy Sinatra’s in her Outside Lands set seems to suggest the singer isn’t afraid of leaning into her Americana roots, and based on her performance this past weekend, we think it’s safe to say she can master any genre she likes. Plus, we certainly wouldn’t be mad about getting more Carpenter-Musgraves collaborations in the future.

Photo by Daniel DeSlover/ZUMA Press Wire/Shutterstock