Blackpink's Jennie swapped stage glamour for a tailored blend of military precision and biker rebellion during her headlining set at Lollapalooza 2026. The performance at Grant Park in Chicago on Saturday night showcased an Ann Demeulemeester ensemble drawn from Stefano Gallici's fall 2026 collection, just over a week after the release of her solo single "Less Than a Lover." Main Developments The look centered on a cropped oyster-colored jacket worn open over a black leather bralette secured with a small buckle. Firm shoulder lines, epaulets, silver-toned buttons, and horizontal white bands delivered the regimental reference while keeping the silhouette skin-baring and stage-ready. Below the bralette, Jennie wore loose black leather trousers with a high lace-up cummerbund. A tan belt hung slightly undone down the front, and a black-and-white scarf was tied at her hip, softening the tough biker elements with a fluid, romantic touch. Read also: Why Nike's Floral Air Force 1 Is a Blooming Trend You Can't Ignore Ruffled cuffs pulled over her forearms allowed lace ribbons to trail from her wrists, while a white feathered knit headband with crochet roses sat low across her forehead. Stylist Sam Woolf, known for work with Doechii, Latto, and Bebe Rexha, assembled the complete performance outfit. The Ray-Ban global brand ambassador finished with Ann Demeulemeester's sand-brown Sarith Engineer Biker Boots, a suede style featuring darker rounded toes, low stacked heels, and wide buckle straps. Footwear choices have become a signature element of her 2026 style evolution. Background Gallici's fall 2026 collection for the Belgian-born label paired romantic details with regimental coats, cropped Napoleon jackets, and biker leather. WWD critic Sandra Salibian highlighted the collection's "poetic ruffled blouses" and "stompy boots," elements Jennie condensed into a single performance-ready silhouette. The Sarith boot has been gaining traction across celebrity circles throughout the year. Dua Lipa has repeatedly worn the silhouette in black, while Charli XCX opted for a distressed brown version at Sundance. Kendall Jenner has favored the label's more pared-back Bente boots, signaling a broader trend toward the brand's footwear. 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. Why It Matters Jennie's festival styling demonstrates how runway concepts translate into high-impact performance wear, a crucial bridge between luxury fashion houses and mainstream pop audiences. Her choices carry significant visibility, given her global platform as a Blackpink member and solo artist. The repeated celebrity adoption of Ann Demeulemeester boots signals a sustained moment for the label's footwear beyond its core runway following. Each high-profile appearance reinforces the brand's position in celebrity styling rotations, potentially driving consumer interest in similar silhouettes. What's Next Lollapalooza closes Sunday with Tate McRae and the xx headlining the final night at Grant Park. Jennie's festival appearances this summer have showcased a diverse range of designers, from Betsey Johnson recreations to Ann Demeulemeester's romantic military aesthetic, leaving open questions about which labels will appear in her upcoming performances and promotional cycle for "Less Than a Lover."