The clip, which was shared on TikTok by Aerial Harris, who goes by the username @xoaerialxo on the app, was taken at the “Vogue World” party in New York’s Meatpacking District on Monday, in celebration of Vogue’s 130th anniversary.
In the video, Wintour, who wore a floor-length patterned skirt, a red top, and her signature dark sunglasses for the occasion, could be seen sitting in the front row set up on the cobblestone catwalk, with Lil Nas X next to her on one side and Serena Williams seated on her other.
As the opening notes to the rapper’s song “Industry Baby” began to play, Williams began to clap her hands, while Wintour turned to Lil Nas X, who then began to sing the song from his seat next to her.
The beginning of the performance was met with a brief smile from Wintour, who began to tap her foot to the beat of the song.
The 23-year-old singer, who was dressed in wide-leg silver metallic pants and a matching top bedazzled in sequins, then stood up from his seat as he began to sing the song in earnest.
On TikTok, where the video has been viewed more than 3.4m times, viewers have shared their joy over the video, with many praising Lil Nas X for making Wintour smile, while others expressed their glee over the magazine editor’s dance moves.
“He made Anna smile,” one person wrote in the comments, while another said: “I’ve never seen Anna smile omg.”
“NOT ANNA WINTOUR STOMPING TO THE BEAT!!!” someone else wrote.
The video also prompted one person to suggest that the video captured the closest Wintour has “ever been to letting loose”.
“Anna is lowkey delighted,” one viewer claimed, while another said: “Awww look at her tapping her foot.”
According to someone else, Wintour’s subtle dance moves were proof that she was enjoying herself. “Anna’s foot tapping is the ultimate approval,” they wrote.
Lil Nas X’s performance at the event also proved to be just one reason for Wintour to smile, as another video uploaded by Harris showed the Vogue editor conversing with the rapper as they sat next to one another.
“Safe to say Anna’s a fan,” Ms Harris wrote in the caption of the video.
The video prompted amusement among viewers, with many agreeing that the normally stoic Wintour appeared to be fond of the rapper.
“Why have I never seen Anna this happy or intrigued,” one person noted.
Lil Nas X’s attendance at the Vogue party comes after he made his New York Fashion Week debut earlier in the week when he walked the runway at Coach’s Spring/Summer 2023 show on 12 September.