Chicago's Fashionable City and Travel Guide

What our Favorite Bloggers are Wearing to Lollapalooza

What our Favorite Bloggers are Wearing to Lollapalooza


It’s finally here – Lollapalooza weekend! We’ve got you covered with details on how to successfully conquer Chicago’s biggest music festival. Which shoes to wear, what to pack, which aftershows are going to be amazing, and what you’re wearing (which will help me figure out what I’m wearing). 

Almost everyone is headed to Grant Park this weekend. Meanwhile, at this late hour you may, like me, have no clue what to wear. We’ve rounded up the best festival fashion inspiration from local bloggers and Lolla attendees. Enjoy!

NOTE: This post will be updated throughout the weekend with more photos!

A photo posted by KATELYN MASEK (@katelynmasek) on


Who: Vlogger and blogger Katelyn Masek

What: This photo is from weeks ago but Katelyn looks ready for now in Free People and Chanel

What to wear to Lollapalooza
Who: Blogger Lauren Nolan of Lake Shore Lady

What: Sweet and simple, Lauren looks amazing in the Motel combo – and I love her bucket bag from Rebecca Minkoff!

What to wear to Lollapalooza

Who: Blogger Paige Mariah

What: How cute is Paige in a mix of thrifted and new finds!?

Check back for more festival fashion pics throughout the weekend!

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