What To Wear To Lollapalooza In 2025
Photo Credit:@michemingg
Every year, Lollapalooza rolls into Chicago and the same question hits me like a bass drop: what am I wearing?
Because listen, Lolla is not just about the music—it’s about the fits. And while I’m not showing up in a mesh bodysuit and combat boots (no shade if you are), I still want to feel like me in the crowd. Cute, comfortable, and prepared for whatever the weather decides to do between 2 PM and midnight.
So whether you’re there for Tyler The Creator or just the vibes, here are some outfit ideas that won’t leave you sweating through denim or Googling “how to fix blisters in a porta-potty.”
And yes, these are real outfit combos. Not costume-y. Not try-hard. Just pieces you’ll actually wear again—and feel good in while dancing in the dirt.
1. Oversized Graphic Tee + Bike Shorts + Cool Sneakers
Easy to move in, looks effortless, and hides all the sweat zones. Bonus points for a bold tee.
Spice Girls Doodles Merch Tee
DAYDREAMER
$92
Neoprene Capri Legging
Commando
$128
Field General Se Sneaker
Nike
$100
2. Mesh Top + Bralette + Cargo Pants + Chunky Sandals
A little edgy, a little breathable, and the pockets? You’ll thank yourself.
Amazon
Rhinestone Body Chains Long Sleeve Crop Top
$22.99
Amazon
High Waisted Cargo Pants
$29.99
Amazon
Memory Foam Insole Sandals
$49.90
3. Denim Shorts + Crochet Tank + Bucket Hat
Cute and classic but still has that ‘I go to festivals’ feel.
Amazon
V-Neck Crochet Crop Top
$14.99
Amazon
Levi's Women's 94 Baggy Shorts
$59.50
Amazon
Crochet Bucket Hat
$14.99
4. Romper + Fanny Pack + Sunglasses
The one-and-done look that works when you don’t want to overthink it.
Cupshe
Bluebell Skies Denim Romper
$32.99
Amazon
Shoulder Bag Fanny Pack
$24.83
Amazon
Aviator Sunglasses
$19.99
5. Sports Bra Top + High-Waisted Linen Pants + Platform Slides
Balanced, breezy, and very much I do yoga but also go to concerts.
Tie Front Bandeau Crop Top and Wide Leg Pants Set
$38.99
Crocs Brooklyn Buckle Low Wedge
$59.95
6. Two-Piece Matching Set + Sneakers + Claw Clip
It looks like you tried, but you didn’t. Bonus: easy bathroom trips.
Amazon
2 Piece Sets Summer Ribbed Knit Crop Tank Tops Wide Leg Pants
$53.99
adidas Unisex-Adult Samba Indoor Sneaker
$89.95
7. Strapless Bodysuit + Maxi Skirt + Converse
Keeps you cool but still feels styled—great for dancing and moving around.
Second Skins Strapless Bodysuit
Only Hearts
$80
Maddox Skirt
BY.DYLN
$79
Chuck Taylor All Star Sneaker
Converse
$60
8. Halter Top + Parachute Pants + Mini Backpack
Trendy but wearable. Parachute pants = air flow + fashion.
Old Navy
Double-Layer Halter Top
$19.99
High Waisted Wide Leg Pants
$32.99
9. Oversized Button-Down (Worn Open) + Bra Top + Denim Shorts
Throw it on when the sun hits or tie it around your waist. Lightweight but looks intentional.
Oversized Button Down Shirt
$35.99
Bandeau top
$36.99
Denim Shorts Mid Waist Ripped Distressed
$31.99
10. Unitard + Oversized Jersey + Socks + Sneakers
Unexpected but works. Add hoop earrings or sunnies to balance the sporty vibe.
Ribbed Square Neck One Piece
$14.99
Crochet Jersey Shirts
$35.99
Vintage Tennis Sneakers, Casual White
$89.95
11. Satin Cami + Baggy Jeans + Statement Belt
Effortless festival glam with minimal effort. Looks great with a messy bun and red lip.
Old Navy
High-Waisted Baggy Wide-Leg Jeans
$49.99
12. Crop Tank + Tiered Mini Skirt + Combat Boots
Flirty meets functional. You can dance in it and stomp through mud.
Workout Cropped Tank Top
$27.89
Ruffled Tiered Skort
$34.99
Chelsea Combat Boots
$52.99
13. Baby Tee + Loose Joggers + Crossbody Bag
Underrated combo. Comfort first, but it still looks intentional.
Basic Tee Tight Fit
$16.99
Barrel Leg Sweatpant Drawstring
$36.99
Small Woman's Crossbody Bag
$119
14. One-Shoulder Top + Paperbag Shorts + Slide Sandals
A cute silhouette switch-up if you’re tired of denim.
Sleeveless One Shoulder Slim Fit Shirt
$19.99
Plus Size Elastic Waist Scallop Trim Flowy Wide Leg Shorts
$25.99
15. Ribbed Tank Dress + Baseball Cap + High Tops
Feminine but chill. The hat gives it a little edge—and helps with sun protection.
Bodycon Dress
$27.99
Buckle Open Toe Ankle Strap Platform Wedge Sandal
$46.95
Yankees Branson Cap
$34.99
16. Tube Top + Pleated Tennis Skirt
It’s giving Y2K, but toned down and functional. Add a crossbody for balance.
Tube Tops Bulit in Bra
$26.89
Tennis Skirt for Women with 4 Pockets
$27.99
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