STYLES’S confidence is on full display the day after the fitting, which finds us all on the beautiful Sussex dales. Over the summit of the hill, with its trees blown horizontal by the fierce winds, lies the English Channel. Even though it’s a two-hour drive from London, the fresh-faced Styles, who went to bed at 9 p.m., has arrived on set early: He is famously early for everything. The team is installed in a traditional flint-stone barn. The giant doors have been replaced by glass and frame a bucolic view of distant grazing sheep. “Look at that field!” says Styles. “How lucky are we? This is our office! Smell the roses!” Lambert starts to sing “Kumbaya, my Lord.”

Hairdresser Malcolm Edwards is setting Styles’s hair in a Victory roll with silver clips, and until it is combed out he resembles Kathryn Grayson with stubble. His fingers are freighted with rings, and “he has a new army of mini purses,” says Lambert, gesturing to an accessory table heaving with examples including a mini sky-blue Gucci Diana bag discreetly monogrammed HS. Michele has also made Styles a dress for the shoot that Tissot might have liked to paint—acres of ice-blue ruffles, black Valenciennes lace, and suivez-moi, jeune homme ribbons. Erelong, Styles is gamely racing up a hill in it, dodging sheep scat, thistles, and shards of chalk, and striking a pose for Mitchell that manages to make ruffles a compelling new masculine proposition, just as Mr. Fish’s frothy white cotton dress—equal parts Romantic poet and Greek presidential guard—did for Mick Jagger when he wore it for The Rolling Stones’ free performance in Hyde Park in 1969, or as the suburban-mom floral housedress did for Kurt Cobain as he defined the iconoclastic grunge aesthetic. Styles is mischievously singing ABBA’s “Gimme! Gimme! Gimme! (A Man After Midnight)” to himself when Mitchell calls him outside to jump up and down on a trampoline in a Comme des Garçons buttoned wool kilt. “How did it look?” asks his sister when he comes in from the cold. “Divine,” says her brother in playful Lambert-speak.

As the wide sky is washed in pink, orange, and gray, like a Turner sunset, and Mitchell calls it a successful day, Styles is playing “Cherry” from Fine Line on his Fender acoustic on the hilltop. “He does his own stunts,” says his sister, laughing. The impromptu set is greeted with applause. “Thank you, Antwerp!” says Styles playfully, bowing to the crowd. “Thank you, fashion!”

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Watch Harry Styles Sing an Acoustic Rendition of “Cherry” in Vogue’s Cover Video: