The Best Guide to Lollapalooza

How to Dress for Lollapalooza


what to wear to Lollapalooza
Local blogger Blake (IG: @BlakeVonD) brought her enviable style to Lolla.

What to Expect at Lollapalooza

“I feel like nondescript meat being pushed through a grinder. The sun’s especially angry today, and the normally welcome breeze from Lake Michigan feels more like a waft of heat from an open oven door. It burns my shoulders as my arms slap into the bodies of dirty, sweaty strangers. Are these people drunk? It’s not even noon. I’m starting to believe every terrible thing I’ve heard about Lolla is true.” – Me, heading into my first Lollapalooza (2015).

Oh, what a bougie brat I was, working my first big festival, smuggling in a DSLR camera because my photo clearance was denied. My ticket, food, and drinks all comped. Still, I found a way to complain. I can proudly say, now with three consecutive years of Lollapalooza under my belt, nothing has changed. I still complain. But not as much. Lolla is what it is, and once you understand what to expect, it’s a great time. An unforgettably amazing time, actually!

Allow me to resurrect this festival analogy: In a family of festivals, if Riot Fest is your brooding hermit of a brother, Spring Awakening your hyper little sister, Mamby on the Beach your mellow best friend, then Lollapalooza is your mom. She’s not a regular mom. She’s a cool mom. Fun but dependable and surprisingly LIT after a few drinks.

If you’re expecting a sea of drunks and burnouts, make a left at the next exit for Riot Fest. Lolla’s all about the kids, ya’ll! And most of them are hoping to see Post Malone while riding on the shoulder of their dads who are super stoked over LL Cool J (and secretly Logic). Point is, there’s something for everyone, so expect a variety in the crowd and on the stages.

Now that you’ve figured out where you are, let’s discuss what to bring.

How to dress for Lollapalooza

Lollapalooza Survival Guide: What to Pack and How to Dress

What Should You Bring

Make Like Baloo the Bear: Only bring the necessities. In three years, I’ve never been to a Lollapalooza that hasn’t ended early because of a rainstorm. That means mass evacuations, everything stops and security escorts 100,000 people out. The saddest sight is watching teens stand in the rain while waiting in line to retrieve their things from lockers. Tip: If it’s in a locker, you probably shouldn’t have brought it to begin with. Leave that makeup kit at home, boo!

Suggestions on what to bring to Lollapalooza:

  • A phone
  • Charging bank
  • Small face towel (you’ll be surprised how often this comes in handy!)
  • Driver’s license (no need for your entire wallet)
  • Cash
  • Lipstick
  • Mirror
  • Facial tissue
  • Sunscreen
  • Sunglasses
  • Poncho
  • A reusable water bottle. And about that…

Evian spelled backwards is naïve: Pack a reusable water bottle. Water ain’t free – ‘cept it is. And you didn’t spend all your money to stand in line waiting for it. This isn’t a survival camp. It’s a music festival. Bring a bottle and fill it up at your leisure. Which reminds me, stay hydrated. Seriously, people are always fainting. Because sun and heat. Don’t be like people.

What to Wear to Lollapalooza

What should you wear? Whatever you want. J/k. Don’t do that. Whatever you choose to wear, however, needs to be comfortable. As comfortable as pajamas but as chic as a drifter on her way to a job interview. Or like a desert dweller who recently found the lost luggage of a wealthy jet-setter on the side of the road. If none of that makes sense, let’s look at a few photos.

what to wear to lollapalooza
We’re not sure how but he manages to make overalls look as dapper as a three piece suit. Kudos!

what to wear to Lollapalooza

what to wear at lollapalooza
Sometimes all you need are jeans and a smile.

what to wear to Lollapalooza
Summer dresses and boots for the win!
what to wear to lollapalooza
One year, Zeik McCarter of band Con Brio started Saturday off repping the Chicago Bulls well from head to toe.

LollapaloozaWhat to Wear to Lollapalooza, a few Suggestions:

  • No Heels Zone. They Know Betta. Word to Sremmurd.
  • No flip flops either.
  • For the first time ever, I’m suggesting a sweater/kimono/something because temps may drop into the fifties. (Can you believe it? Thanks Chicago.)
  • No brimmed hats. I know some girls love their hats and look great in them, but do you really want to wear it all day? Don’t be mad. You look really cute in it, though. Okay, fine. Wear it if you want.
  • No big purses. Absolutely not.

Final tips

Download the app for up-to-the-minute alerts and follow Lollapalooza on Twitter for the same info.

AND OF COURSE, follow on Instagram for a virtual step inside of VIP!

Have fun, boo!

All photos taken by Kari Herrera of

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