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Lollapalooza 2026’s Best Looks: Charli xcx’s Vintage Saint Laurent Heels, Tate McRae in All White and a Military-Jacket Revival

Four days in Grant Park produced a Pleats Please pink hoodie, a Valentino-clad Sombr and a Nylon No. 1 for the headliner who wore the mess best.

August 3, 2026 · 2 min read · No. 0171
Lollapalooza 2026’s Best Looks: Charli xcx’s Vintage Saint Laurent Heels, Tate McRae in All White and a Military-Jacket Revival
Tate McRae closes Lollapalooza in a custom Ludovic de Saint Sernin look, Grant Park, Chicago, Aug. 2, 2026. Getty Images via The Zoe Report · Photo: Getty Images via The Zoe ReportNo. 0171

The best-dressed act at Lollapalooza was the one who looked the most like she’d been out in the rain. Nylon put Charli xcx at No. 1 on its ranking of the festival’s onstage looks, praising her headline set’s opening trench coat and teetering vintage Saint Laurent heels, and a closing look of a tattered white T-shirt, fingerless gloves and an oversized belt. “It’s not afraid to be messy, ugly, dowsed in rain — in fact, it looks better that way,” Nylon wrote.

The Zoe Report catalogs a different part of Charli’s set: a sheer Jing Hé tunic over a Fleur du Mal bra with fishnets, a custom Zana Bayne leather garter, and later a custom handkerchief minidress by the London designer James Walker. She opened with “Rock Music,” according to Rolling Stone, and the heels carry a thread from June, when she sat front row at Saint Laurent’s menswear show in Paris. She also joined Lorde on Thursday for a remix of “Girl, So Confusing.”

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Three trends ran through the weekend, The Zoe Report says: military jackets, lingerie-like layers as the temperature rose, and sunglasses on nearly everyone. Jennie headlined Saturday in the weekend’s leading military look, an Ann Demeulemeester white structured jacket over a black leather bralette and baggy trousers. Nylon called it punk, and said it “moved well with her.”

Jennie in Ann Demeulemeester at Lollapalooza, Grant Park, Chicago, Aug. 1, 2026. Getty Images via The Zoe Report · Photo: Getty Images via The Zoe Report

Sombr took the lace route: a black Valentino lace tank, flared pants and a feather-trimmed military jacket, fitting for one of Valentino’s newest ambassadors under Alessandro Michele. He brought 5 Seconds of Summer out for “She Looks So Perfect.” Lorde kicked off the festival in a bright pink Pleats Please Issey Miyake hoodie over a matching bikini top and black patent trousers. Adéla wore custom pink Christian Louboutin platform boots that matched her hair, Suki Waterhouse a ruffled, feathered pink cape, and Zara Larsson a Y2K striped crop top and denim hot pants.

Sombr at Lollapalooza, Grant Park, Chicago, July 30, 2026. Getty Images via The Zoe Report · Photo: Getty Images via The Zoe Report

Tate McRae closed the festival on Sunday in a white custom Ludovic de Saint Sernin look, a curved-neckline crop top with bodice cutouts and matching pants, with white pumps and a thin gold bracelet. Rain delayed Saturday’s program and cost a few acts their sets, Rolling Stone noted. Charli’s album Music, Fashion, Film, whose era the headline set was built around, opened at No. 3 on the Billboard 200 that week.

Added to the High Grailed archive on October 12, 2026.

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