If you purchase an independently reviewed product or service through a link on our website, Rolling Stone may receive an affiliate commission.
Lollapalooza, the iconic four-day music festival held in Grant Park in Downtown Chicago, is right around the corner. Kicking off this Thursday, July 31, the event promises performances from major artists like Sabrina Carpenter, Olivia Rodrigo, Tyler, the Creator, RÜFÜS DU SOL, and more than 150 other acts.
And let’s be real: Whether it’s your first festival or your fiftieth, what you wear is almost as important as the lineup itself. If you’re still outfit-less for your trip to the Windy City, don’t panic, we’ve rounded up the ultimate Lolla fashion must-haves to save you from hours of scrolling Pinterest for the perfect look.
Unlike Coachella or Tomorrowland, Lollapalooza doesn’t have a specific “look,” which can make outfit planning a bit trickier. Our fashion editors, who are all festival veterans themselves, recommend prioritizing comfort. Think flowy, breathable pieces that move with you. We suggest going towards an effortless boho vibe, but with a modern twist — not full-blown 2014 Tumblr.
What to Wear to Lollapalooza 2025
Maxi skirts, ruffled dresses, bandana tops, and relaxed button-downs are all Lolla-approved staples. We’ve curated a selection of favorites below to help you out. From brands like Hollister, For Love & Lemons, and Amazon, to official merch from headlining artists you can snag ahead of time (no need to waste time in those vendor lines), we’ve got you covered. Shop our top Lollapalooza 2025 picks below.
Best Lollapalooza Outfits for Women 2025
viral trend
Hollister Tiered Maxi Skirt
If you’ve seen the viral clips from the Lumineers tour, then you already know: white maxi skirts are everywhere this concert season. And it makes total sense — they’re comfy, flattering, and somehow look good on everyone. You can snag this one from Hollister for under $45.
editor’s-pick
Hollister Button-Through Sweater Tank
The easiest (and arguably best) thing to pair with a lightweight skirt? A breezy, simple tank. This butter-yellow version, which is the “it” color of the year, is a must-buy.
two-day shipping
Heartloom Lauren Top
With Lollapalooza just around the corner, Revolve is your best bet for last-minute outfits. They offer next-day shipping (starting at $30) and free two-day delivery on most items.
Agolde Parker Long Short
Agolde shorts have been my go-to for years. The fit is reliable, they’re super comfortable, and there’s plenty of room to move without ever feeling restricted. Style them with a bandana top (like the one above), or your favorite artist’s tee (Sabrina Carpenter, anyone?).
on trend
For Love & Lemons Teagan Mini Dress
For Love & Lemons could give a masterclass on festival fashion. Think flowy, fairycore vibes that will last you from the moment gates open to the after-after party.
Olivia Rodrigo World Tour Shirt
What’s more iconic than wearing the tee of an artist performing that day? Olivia Rodrigo headlines Friday, and this official Guts World Tour tee deserves a spot in the crowd — and on you.
ANRABESS Boxer Shorts
Boxer shorts for women are having a major moment right now — from NYC street style to your FYP. Their no-fuss vibe and breathable fabric make them great to try out during a day at Lolla.
Thistle and Spire Smoke Mirrors Bodysuit
I’ve worn this bodysuit to so many festivals — Life is Beautiful (2021), Governor’s Ball (2022), Coachella (2023) — and it never lets me down. It’s secure where it counts (no nip slips here), and worth every penny for a piece you’ll keep reaching for.
Tecovas The Annie Boots
Wearing cowboy boots to a festival just feels right, and the Annie boots from Tecovas are the best of the best.
Topacc Gold Concho Belt
Another must-have? A chunky belt. It pulls everything together, whether you’re rocking a ruffled mini, denim shorts, or a flowing maxi dress.
Best Lollapalooza Outfits for Men 2025
Hollister Boxy Linen-Blend Short-Sleeve Shirt
For guys, you can’t go wrong with a boxy button-down. Wear it closed or open over a white tank, and pair it with cargo or athletic shorts for that effortlessly laid-back vibe.
best-seller
Lululemon ABC Classic Fit Shorts
Speaking of comfort, the Lululemon ABC shorts bring the same fit and feel as their best-selling pants, but in a warm-weather version that’s festival-ready.
Kenny Flowers The Passport To Paradise Shirt
Kenny Flowers knows exactly how to do printed shirts that pop. Ideal for standing out in the crowd, their products come in a wide range of patterns, are breathable enough to dance in (even to dubstep), and, most importantly, are anything but basic.
Skechers Slip-Ins Silver Sneakers
My number one festival rule? Always wear comfortable sneakers. With all the walking — from one stage to the next — you’ll likely rack up between 10,000 and 20,000 steps a day (or more). The last thing you want is to be sidelined by sore feet before the headliner even hits the stage. But supportive doesn’t have to mean orthopedic. These silver Skechers, designed to keep your dogs from barking day one through day four of Lollapalooza, also bring serious style. The sleek, monochromatic color scheme adds a cool, futuristic edge to any outfit, so you’re covered on comfort and fashion. It’s the best of both worlds.
Glitter Mesh Shirt
No festival outfit guide is complete without a glitter mesh top. Wear it solo, layer it up, or grab it in one of the nine other available shades.
fast shipping
Men’s Flamingo Hawaiian Set
Flamingo sets have become a festival staple — and this one from Amazon lets you join the trend for under $40. Which means you’ve still got room in your budget for another rite of passage: vendor merch.
Adidas Clear Crossbody Bag
And don’t forget a clear fanny pack. It keeps your shit safe and venue-approved.
artist merch
Tyler, the Creator Flower Boy Bee Hat
If you want to skip the merch lines (and save some cash), grab this official Tyler, the Creator hat on Amazon ahead of time, no one will know the difference, and you’ll be stage-side before the first beat drops.