Lollapalooza is winding down in Chicago after a massive four days to celebrate the festival’s staggering 25-year presence in the world. We watched on as Grimes stole our hearts while belting out lyrics in Russian, we relived retro rock with the Red Hot Chili Peppers, got political with Vic Mensa when he dedicated “There’s Alot Going On” to the Chicago Police Department, spotted Malia Obama just chilling with her friends like NBD, and Big Grams melted us into puddles when Phantogram’s Sarah Barthel carted around her teacup puppy Leroy (sporting a gold chain and black T-shirt just like Big Boi).
Oh, and did we mention that the party also extended way, way into the night? After hours, we teamed up with the dFm for hangs with everyone from HÆLOS to Dua Lipa and Bastille. The week was four days in the heart of Chicago that showed why Lollapalooza has been a mainstay and is a singular experience that delivers an stunning showcase of not only the best of the best, but the best we haven’t heard of yet.
Of course, when you’re going to see the best that music has to offer, you also have to look your best. We found an array of people that were willing to stick it out through rain, humidity, and endless trekking across Grant Park to make sure they were always photo-ready. From Chicago model Brandon Tyler who sported cuffed jeans with a vintage jacket from local retailer Kokorokoko to NYLON favorite Chairlift, we found a spread of styles that not only looked chic but were ready for the festival’s all-day grind. See some of our favorite looks below.