By Isa Giallorenzo
Are you someone who basically goes to Lollapalooza to people watch, relax, get some sun, discover tasty street foods and do some shopping, having only a vague idea of the bands in the lineup? This guide is for you—remember to save it for next year!
Best Lolla looks
Goodbye flower crowns, hello fanny packs. This year it was more about sporty practicality than bohemian ornamentation. Style DOs: oversized basketball jerseys worn as dresses; matching tops and bottoms. Style DON’Ts: any faux or real fur item; tights; excess of non-breathable fabrics.
Best festival accessory
Yes, the fanny pack. It’s happening. See-through bags in general are also having a moment—very contemporary and practical. A festival accessory that should be happening: visors. They give you shade, don’t take up too much space in your bag and can totally complement fanny packs in a hip revival of touristy must-haves.
Best use of outdated flower crowns
Recycle! Why not put them on your feet as opposed to your head?
Best place to have your picture taken for Instagram
This spot had the Buckingham Fountain, the Lollapalooza inflatable logo, and the Chicago skyline in the background, plus some cute square framing, readily formatted for your Insta feed.
Best place to people-watch
Arguably also the best place to people-watch in the world: one of the benches by the Buckingham Fountain. Highly entertaining, and somewhat relaxing.
Best place to chillax
The Farmer’s Market Area. There’s a lawn where you can lie down and take your shoes off, a picnic area, and the square surrounding the Lincoln statue with plenty of seating, right by one of Lolla’s best stages. This year the Budweiser tent was there as well, providing a very refreshing water mist—among other favors.
Best place to eat delicious non-gross street food
Again, at the Farmer’s Market. The Seedling (seedlingfruit.com) blueberry smoothie made with cider was in itself the best reason to attend Lolla this year. A close second was the Brunkow Cheese (brunkowcheese.com) Brazilian-style grilled cheese on a stick and their fresh Caprese salad. Fortunately both vendors also sell their local delicacies in the Lincoln Park Farmers Market and in select city shops.
Best shopping opportunities
On Green Street (just south of the Farmer’s Market), Teysha (teysha.is) sells handcrafted fair-trade boots and flats made in Guatemala, with a special fest price. Their footwear is incredibly soft, unique and colorful—with a delightful leather smell. The Hot House Market (hothousemarket.com) carries a well-curated selection of vintage clothing, including a ton of cute denim shorts perfectly suited for the festival. And last but not least, the merch tents by the Buckingham Fountain always deserve a visit—this year’s adorable bear commemorative tee was illustrated by the artist “Timber!” (still for sale at store.lollapalooza.com)!
Best design solution
Bringing your own hammock. Unlike the ones at the official hammock lounge, it will always be available to you, and close to your stage of choice. Unlike a chair, it’s easy to carry, and unlike a mat, it offers back support.
Best festival favor
The Sprint cell-phone covers. They allow you to conveniently hang your phone on your neck and protect it from the elements, while still having access to your touch screen. Genius.

Journalist Isa Giallorenzo was born in São Paulo, Brazil and has elected Chicago as her beloved home since 2009. She runs the street-style blog Chicago Looks and wants to see this town become one of the fashion capitals of the world.