“Fashion may be my full-time job, but I’m a huge music fan and try to expose myself to as many shows as I can. Nothing beats the energy and excitement of a good concert. My friends and I have been taking trips to summer festivals for about six years now, and those trips are something I look forward to all year. This year, we chose Lollapalooza—with the city of Chicago as the perfect backdrop to take it all in. Scroll through to see weekend highlights from the Second City—coming in first for good times!”

-Ashley Calandra

VALENTINO Jacket / SAINT LAURENT Sleeveless Shift Dress / JENNIFER FISHER Jewelry

The first thing we did when we touched down in Chicago was head straight to Freds.

SHOP ALL JENNIFER FISHER Rings and Bracelets CHECK OUT The Freds Chicago Menu

We sat outside on the terrace and ordered my personal favorite, the caprese salad. Not pictured: the truffle fries—they were gone by the time we took this photo!

First stop at the festival was Father John Misty. Then we headed over to see MS MR, who played such a fun set. We caught up with Lizzie and Max afterwards and talked about their sartorial festival choices. “For us, it’s an opportunity to be the most exaggerated and bombastic version of our normal selves,” Lizzie told us. “There’s a freedom and heightened sense of individuality and experimentation when it comes to festival wear that is incredibly exciting and fun.” 


Possibly the most stylishly accessorized hand in the crowd? With Jennifer Fisher jewelry…I’d like to think so.

STELLA MCCARTNEY dress worn as jacket / RE/DONE Denim Shorts / STELLA MCCARTNEY Baby Bella Shaggy Mini Tote 

I couldn’t resist this Stella McCartney shirtdress that I wore open, styled as a jacket, and paired with my fringe Stella bag. Only fitting since Paul McCartney headlined the festival!

KAREN WALKER Harvest Sunglasses / SAINT LAURENT Fringed Bucket Bag

After a good SPF, festival must-haves that top my list include oversized sunnies and a hands-free bag.

Win Butler photographed by Chad Kamenshine.

We decided to keep the music streak going post-Lollapalooza day one and grabbed drinks at the Virgin Hotel where Win Butler from Arcade Fire was spinning as DJWindows98. Arcade Fire is one of my all-time favorite bands so this was a solid highlight of the weekend. 

RAY-BAN Aviator Sunglasses / HOURGLASS Opaque Rouge Liquid Lipstick

We started off day two backstage at The Givers set. It was pretty amazing to watch the band perform from so close and be able to look out on at the crowd and see what great energy everyone had.

Other music highlights from the day were: Walk The Moon, Tame Impala, Kid Cudi, and of course Sam Smith who sang a rendition of “Tears Dry On Their Own” by Amy Winehouse.

In true Windy City fashion, a major storm hit the area. Luckily, we were still able to catch a lot of our favorites like: George Ezra, Albert Hammond JR, Lord Huron, and of Monsters and Men.

Florence Welch—who looked so chic in a metallic pant suit—said it best: “It’s us against the storm.” Judging from the enthusiastic crowd, I think we won this weekend.

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