Lollapalooza Chicago 2026 kicked off Thursday with a number of acts taking the stage, culminating with headliners Lorde and John Summit. With a wide range of artists and genres at the festival, several fashion aesthetics could be seen onstage. See some of the boldest moments from Day One below.

Rhian Teasdale of the English indie rock band Wet Leg opted for the sport-inspired Leather Soccer Flat Tall boots from Empty Behavior, which is described as an experimental footwear brand. The dark leather boots had a futuristic aura to them, with linear detailing and a wide knee-high shaft. The shoes accompanied a silver chainmail set featuring a miniskirt and cropped top with the number 50 in yellow on it.

Ross Cullen of the post-punk industrial dance duo Chalk, which was formed in Belfast, Northern Ireland, brought a Goth aesthetic to the Lollapalooza stage. For footwear, the musician opted for an edgy boot from New Rock; the style featured heavy chain detailing and more metallic hardware. The shoes went with black shorts and a distressed black Adidas shirt with metallic details.

Felip Jhon Suson of the Filipino boy band SB19, who professionally goes by Ken in the band and Felip as a solo artist, performed in a dramatic Rick Owens shoe. Suson showcased the Mega Bumper Geobasket sneakers, which feature a platform sole and extended tongue. The black and off-white shoes accompanied black leather pants, a black top and an embellished off-white jacket.

Michelle Buzz of the American alternative pop duo Haute & Freddy brought a Victorian shoe look to the stage with a calf-height white boot featuring a lace-up shaft, sculptural block heel and perforations. The boots rounded out a look including floral tights, striped lace-trimmed shorts and a brown patterned top with puffed sleeves; both the top and shorts also had crisscross lacing details.