Lollapalooza 2026: The Biggest Celeb Fashion Flops

And that's a wrap on Lollapalooza! The second-biggest U.S. music festival after Coachella happened from July 30 to August 2, 2026, in Grant Park, Chicago, featuring headliners like Lorde, Charli XCX, the Smashing Pumpkins, the xx, Olivia Dean, Jennie, and Tate McRae. This year's four-day extravaganza featured everything from electrifying performances to unexpected duets and memorable fashion moments. Charli XCX took the stage during Lorde's headlining set for a remix of their collaboration song "Girl, So Confusing," while Sombr surprised the crowd by bringing out 5 Seconds of Summer for a live performance of their 2014 hit "She Looks So Perfect."

Fashion-wise, Zara Larsson, Asha Banks, and Suki Waterhouse led the pack with some of the festival's standout ensembles, while a handful of stars — including Jennie and The Neighbourhood's Jesse Rutherford — unfortunately missed the style memo. Below, take a look at the celebrities whose festival looks totally missed the mark at Lollapalooza 2026.

Headlining Day 3 of this year's Lollapalooza, Blackpink's Jennie Kim couldn't decide on just one trend with her custom ensemble by Belgian designer Ann Demeulemeester featuring several different elements. She wore a military cropped jacket that was left open over a black leather bralette and denim hot pants. She then added oversized trousers on top, which she paired with a skinny suede belt and a silk scarf tied at her hip. Finally, she finished off the ensemble with a feathered headpiece and a pair of brown suede boots. Unfortunately, there was just a bit too much going on at once.

We're not sure which is worse: the jersey-and-floral shirt combo or the mud-stained jeans. Billie Eilish's ex-boyfriend, Jesse Rutherford of The Neighbourhood paid homage to Chicago by trading his signature leather jacket for a Chicago Bulls merch during the band's Lollapalooza 2026 performance. However, rather than pair it with a simple tee, he put his own twist by layering his jersey over a white floral button-up and distressed jeans. At the very least, he made sure to keep the color palette cohesive, so the outfit wasn't a total disaster. But combined with the mud-stained pants, the whole look simply felt messy.

While we're absolutely digging her statement tee ("God forbid a girl crashes out," printed in all caps), Jordin Sparks' Lollapalooza outfit was very much giving Gen Z energy — and not in the most flattering way, either. The singer and former "American Idol" winner appeared onstage during artist Avello's set to perform their new single "We Own the Night" as a guest performer. Seen above, she paired the statement tee with matching cutout arm sleeves with ribbons, plus cargo pants, and lace-up boots. No offense to Jordin, but she looked like a 30-year-old dressing up as a teen.

Slayyyter (real name Catherine Grace Garner) seemingly confused Lollapalooza for a fishing trip with her Midwest-inspired outfit consisting of a corset, a plaid shirt, and hot pants adorned with cute fish keychains across the front. TBH, it almost worked, if not for the sheer mesh panels of her corset that threw off the look completely. "The look today was definitely inspired by the outdoors," according to Slayyter's stylist, Hunter Clem, who revealed that the "Gas Station" singer styled the shorts herself (via Instagram). "It's very sexy and very, like, powerful, and a bit also leaning into the St. Louis of it all, so there's some camp." Sure!

What in the Coachella is going on here?! Indie singer Claire Rosinkranz looked like she wandered onto the wrong festival grounds with her boho-inspired look during her Lollapalooza 2026 performance. She opted for a white knitted set from Hollister consisting of a high-neck top with matching short shorts. She then accessorized her lewk with a chunky necklace, a matching turquoise chain belt, and some silver arm cuffs with matching jewelry. Even the hair was giving Coachella — all she was missing were a pair of cowboy boots, a wide-brim hat, and a fringe jacket.

Look, she's certainly got the body-ody. But Jadagrace's lewk for Party O2's Lollapalooza performance with her musical partner, Coy Stewart, came across as cheap and flashy rather than edgy. The 26-year-old artist sported a baby tee with camo panties and neon pink fishnet stockings that stretched all the way up across her thighs and hips. She completed her ensemble with military boots, a fishnet arm warmer, and a pair of cool-looking shades (to be totally fair). Judging by her outfit, her shirt should have said "A COMPLETE MESS" instead of system.