Jennie brought Ann Demeulemeester’s romantic military language to Lollapalooza 2026, balancing cropped regimental tailoring with black leather layers, feathered accessories and the label’s Sarith engineer biker boots.

The Blackpink member headlined the festival’s third night at Grant Park in Chicago on Saturday night, just over a week after releasing her latest solo single, “Less Than a Lover.” For the set, she wore a look drawing from Stefano Gallici’s fall 2026 collection for the Belgian-born label.

Jennie left the cropped oyster-colored jacket open over a black leather bralette fastened with a small buckle at the center. The jacket was cut with a firm shoulder line and epaulets, while rows of silver-toned buttons and horizontal white bands brought in the regimental reference.

Below the bralette, Jennie wore loose, black leather trousers with a high, lace-up cumberbund. She left a tan belt slightly undone, letting it hang down the front, and tied a black-and-white scarf at her hip.

Jennie softened the military and biker references with Sann ruffled cuffs, pulling them over her forearms and letting the lace ribbons trail from her wrists. She wore the label’s white feathered knit headband with crochet roses low across her forehead, keeping her soft waves in place. Sam Woolf, who also has also worked with Doechii, Latto and Bebe Rexha, styled the look.

For fall 2026, Gallici paired the same romantic details with regimental coats, cropped Napoleon jackets and biker leather. In her WWD review, Sandra Salibian pointed to the collection’s “poetic ruffled blouses” and “stompy boots.” Jennie condensed those ideas into a cropped, subtly skin-baring performance look.

The Ray-Ban global brand ambassador finished the look in Ann Demeulemeester’s sand-brown Sarith Engineer Biker Boots, a suede style with darker rounded toes, low stacked heels and wide buckle straps. The style joins a growing run of Ann Demeulemeester boots in celebrity wardrobes this year. Dua Lipa has repeatedly worn the Sarith silhouette in black, while Charli XCX chose a distressed brown version at Sundance. Kendall Jenner has also favored the label’s more pared-back Bente boots.

Earlier in the week, Jennie joined Tame Impala in Boston for their first live performance together of “Dracula,” wearing a recreation of a Betsey Johnson spring 1999 design with Veronica Beard Analita patent leather halter sandals. Her Saturday set followed a rain-delayed start at Grant Park. Lollapalooza closes Sunday with Tate McRae and the xx headlining the final night.