Outfit Inspiration

30 Shoes that will Keep Your Feet Comfy and Cute at Lollapalooza

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You didn’t wait this long, fork over a month’s worth of brunch money, have the Chicago skyline painted on your nails, and dye your hair three different colors only to stumble around Lollapalooza in painful, albeit cute, shoes. I get it. There’s a catastrophic conundrum going on here. Looking good vs being able to walk from one stage to the next without keeling over in pain into a pool of your own hurt tears. I understand. Really, I do. But, girl, we have options.

There are tons of shoes that fit the requirements of being both fierce (I’m sorry for saying fierce but alliteration) and functional. Did I mention frugal? Because it is possible to find quality footwear at a cost that doesn’t fight for space with your rent money. Let’s be honest, whatever you wear will probably look like trash come Monday anyway. Find something affordable – and preferably washable.

So where are these fabulous shoes?

From a pool of hundreds, here are 30 pairs of my favorite fest friendly footwear (ALLITERATION!!!). Espadrilles, Oxfords, ankle boots, sneakers, flats, and sandals, all reasonably priced, all currently available. Inspired? Shop below.

What Shoes to Wear to Lollapalooza: The Ultimate Guide

What shoes to wear at Lollapalooza

  1. Bucketfeet Pineappleade Gold | 2. Converse Chuck Taylor Low Sneaker | 3. Adidas Originals Women’s Superstar Casual Athletic Sneaker | 4. Tory Burch Huarache Slip On Sneaker Golden | 5. Adidas Originals Extraball Neon Faux Leather Sneakers

What shoes to wear to Lollapalooza

  1. BDG Leyla Sandal | 2. Circus by Sam Edelman Chandler Platform Sandal | 3. Sam Edelman Gia Knee High Fringed Metallic Leather Sandals | 4. Marni Colorblocked Flat Platforms | 5. Schuts Erlina Sandal

What shoes to wear to Lollapalooza

  1. Kenzo Tiger Logo Suede Espadrille | 2. Soludos Classic Stripe Espadrilles | 3. Rebecca Minkoff Gilles Espadille Flat | 4. Castaner Jean Canvas Espadrilles | 5. Cynthia Vincent Farie Espadrille Flat

What shoes to wear to Lollapalooza

  1. Cole Haan Zerogrand Perforated Oxford | 2. Shoes of Prey Floral Print Cutout Oxford | 3. The Office of Angela Scott Striped Patent Cork Oxford Zebra | 4. Matisse Coconuts by Matisse Cha Cha Cutout Oxford | 5. Rebecca Minkoff Maddie Ankle Strap Oxfords

What shoes to wear to Lollapalooza

  1. Robert Clergerie Ankle Boots | 2. Free People Brooks Ankle Boot | 3. Jeffrey Campbell Carina Ankle Boot | 4. Velia Flat Peep Toe Booties with Wing Detail | 5. Jeffrey Campbell Deep V

What shoes to wear to Lollapalooza

1. Ras Babette Fringe Flats | 2. ASOS Lace Up Flats | 3. Melissa Campana Saptilha Jelly Flat | 4. Marc by Marc Jacobs Women’s Rue Slip on Loafer | 5. Tory Burch ‘Reva’ quilted ballerinas

Kari Herrera is the creator of Chicagoings.com, Chicago’s indie city guide and blog. She often writes about the city’s points-of-interest as experienced by a local. She is a Social Media Marketing Manager and freelance writer. When she’s not working, Kari donates much of her time to the education of French-speaking immigrants in Chicago.

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