The Best And Worst Dressed Stars At Lollapalooza 2026

There are plenty of reasons to come to Chicago — whether it be for the Christkindlmarket, Cloudgate, a Bulls game, and naturally, the hot dogs. However, it's hard to deny that the busiest weekend the Windy City usually faces (as evidenced by how difficult it becomes to navigate traffic, book a hotel, and catch an Uber) is undoubtedly the Lollapalooza Music Festival.

The event comes from nomadic origins, establishing its annual partnership with the city of Chicago in 2005. It ignored genre divides, embracing artists from across the musical spectrum and putting names such as Lady Gaga, Daft Punk, Radiohead, Rage Against the Machine, and Olivia Rodrigo among an eclectic compilation of drastically different top performances over the years. The 2026 edition of the festival was no different, bringing fans of The Smashing Pumpkins and Olivia Dean together around the same stage. While attendees buy their tickets in anticipation of the music, internet users watching the livestreams get to consume the best (and worst) of what these artists' stylists have to offer.

As someone who was in the city that weekend, I can attest to the fact that Lollapalooza 2026 was wet, humid, and erratic. Hit with thunderstorms and an 86-degree high, dressing to impress may have been a liability for some, and the perfect call for others. A musical performance is almost a plate-spinning act of vocals, dance, and costume — and while some artists on this list managed to hit a high note, others visually fell flat.

Swedish pop star Zara Larsson has been running a victory lap all of 2026, and her Lollapalooza 2026 performance was no different. Her fifth studio album, "Midnight Sun," came out early fall of 2025, but the "Lush Life" singer has successfully solidified her place as one of the top artists of the summer with her stunning, almost Lisa Frank-esque aesthetic that is both nostalgic and groundbreaking among her peers. This look may be simple in its components, but the color scheme, silhouette, and viral makeup by her signature artist Sophia Sinot embody all the best parts of her most recent tour.

Blackpink member Jennie Kim went solo for Lollapalooza 2026, but she should have consulted the band's stylist when it came to her outfit. An old-fashioned military jacket hung off her shoulders, showing off a leather bralette and a matching leather lace-up waist trainer and pants. Accessorizing with some frilly gloves and a feather crown on her head, the whole outfit seems aesthetically confused. The leather outfit in isolation was not particularly offensive, but in combination with the coquette-ish accessories, the look is arguably worse than Jennie's greatest regret.

"Revolving Door" singer Tate McRae is known to have some outfits that missed the mark, but her Lollapalooza 2026 look is one of the best from the festival. Throughout the show, bits and pieces of the look were shed, going from a white tank top with interesting cutouts and low-rise jeans, to a matching skirt, to some hot pants. Although simple in concept, the evolution synced up perfectly with her set, ending the night by diving into a pool of gold paint and posing in a shimmering, statuesque pose. Her costume was essentially performance art, which elevates it from its simplicity entirely.

Jordin Sparks hasn't seen much of the limelight since winning American Idol in 2007, but the "No Air" singer may have tried to reinvent her look at Lollapalooza 2026. Donning a "God Forbid a Girl Crashes Out" graphic tee layered over a pink mesh top, and dark denim cargo pants with combat boots, the outfit feels painstakingly Gen Z despite her album "Battlefield" being older than most members of the generation. It takes nothing away from her powerful lyricism and vocals, but it does miss the mark of what a younger audience is expecting.

Considering Slayyyter one of the best dressed of Lollapalooza 2026 may be a bit of a controversial take, but considering her strong emphasis on her Midwestern roots, every attendee I know was absolutely smitten with this look. Almost channeling a Missourian Vivienne Westwood with her cropped flannel over a constrictive nude corset, the whole outfit got a cheeky flair with fish lures draped along her waist. In a post to Instagram, her stylist Hunter Clem described the look as "... definitely inspired by the outdoors," including a bedazzled fish purse.

Jesse Rutherford of The Neighborhood may have attempted to bring a similar Midwestern vibe to his Lollapalooza 2026 look, but unfortunately may have gone a little too touristy. The Bulls jersey over a red rose printed button-up, styled with a pair of dirty ripped jeans, felt trashy in the worst way — and almost a bit too on the nose. Considering the broody lyrics of "Sweater Weather" and "A Little Death," it would have made more sense to lean into the darker, grungier outfits in his wardrobe. Regardless, Go Bulls!