17 Pitchfork Music Festival Street Style Photos Because Festival Fashion Is About More Than Flower Crowns

For the past four years, I have been a vendor at Pitchfork Music Festival in Chicago. Music festival fashion is more challenging to pull off than you may think. Outdoor music festivals mean big crowds, lots of walking, and a chance of anything when it comes to weather (which this year included a massive thunderstorm). Suffice it to say, I have a lot of respect for those who maintain their personal style in the process.

Every year, I swoon over the festival street style and I anxiously await to see if any of my personal favorite looks made it onto the many sites that do style recaps of the festival. But one thing I always notice is that some said style recaps seem to lack the wide array of sartorial choices that I observe walking by my vendor table every year. Each season, I see babes of all genders, races, and sizes looking festival fresh so I wanted to capture an inclusive range of street style festival photos.

While I certainly saw a lot of high waisted jean shorts, flower crowns, and halter tops, I wanted to capture the looks that stood out from the crowd — some of which made me gasp when I saw them, prompting me to chase folks down to take their photo. Consider your summer festival inspiration set.

Images: Alysse Dalessandro

by Alysse Dalessandro

Nana & Darrah

I got all of the ’90s feels when I saw Nana and Darrah walking by my booth. I loved Nana’s black lipstick and crop top and Darrah’s buns and black and white button up.

Instagram: withoutfurtheradu (left) & darrah23 (right)


Kara was the first person that I stopped and when I asked to take her photo, she replied, “This is my dream!” Of course, stopping her was a no-brainer — she was giving me a very My So-Called Life vibe that I just had to capture.

Instagram: memoiirez


Full disclosure: Britt is one of my best friends. However, she is also an amazingly talented arts and culture writer and known as one of Chicago’s most stylish women. Britt is my muse as a designer and she represents everything that I love about Chicagoan fashion — she is confident, bold, and fiercely true to herself.

Instagram: britticisms


I was lucky enough to snap this photo of Monique right before the festival was almost evacuated because of a thunderstorm. From her red lips to her beehive hair, I was crushing on everything about this babe. I need this lollipop print dress ASAP.

Instagram: m0niquegee

Joshua & Joshua

When I saw Joshua and Joshua walk by my booth, I did an internal scream of glee because of how much I loved their looks! They both reminded me why I love fashion. I will probably never forget that FAKE Louis Vuitton bag. And while I didn’t capture their photo every day of the festival, I very well could have because they killed it every single time.

Instagram: close_your_gap (left) & lobotomyblues (right)


When I saw Riley, I loved her style and I had to know where she got this amazing bag that says “YOU ARE NOTHING WITHOUT FEMINIST ART.” Talk about a statement bag! When she told me that the bag was from radical bookstore Blue Stockings in New York, I knew I had a new destination to visit next time I’m in N.Y.C.

Instagram: theselilnotes


I knew as soon as I saw Katie from across the tents that I had to capture this look because I know my calculus, and U + ME really does equal us. Shout out to Katie for looking this good post thunderstorm.

Instagram: mcdeviance

Chanelle & Ashlyn

I stopped Chanelle and Ashlyn because I love how they elevated festival fashion. Chanelle’s crochet dress paired with that massive gold choker was such a statement and I loved Ashlyn’s gladiator sandals and bright printed halter top.

Instagram: chanellicapickles (left) & ashmoxie (right)


I brought along my intern to help me at Pitchfork and she had never been to a festival before. When she showed me how she paired one of the tanks from my line with this black and white skirt for a badass punk look, I was feeling like a proud fashion mom.

Instagram: elizasvon


I am always on the lookout for a good crop top look and Jovan’s teal maxi skirt paired with this bright graphic crop definitely caught my attention. When I showed her the photo I took of her she replied, “Oh yeah, I look fierce.” And yes, she sure does!

Instagram: jovan_keepmovin

Lisa & Justin

Lisa and Justin are festival aficionados, as they both write about music for the Chicagoist, where Lisa is also the editor. I spied Lisa’s purple hair from across the room and loved how she and her beau Justin were still sporting all black in the Chicago heat. That is dedication to a look.

Twitter: lisawhite (left) & justinstrange (right)


In Claire’s Instagram bio, she describes herself as a “feminist grrly metal witch,” and that aesthetic is exactly the reason that I had to capture her amazing festival look. Her expression (and actually the guy in the background’s too) really says it all when it comes to the power of this look.

Instagram: snakekittyyy

Parri & Lauren

I love when friends coordinate completely effortlessly and Parri and Lauren really did just that. I adore the simplicity of their black crop tops paired with these seriously lust-worthy ’90s printed midi skirts. Also, even their poses match perfectly together. Swoon.

Instagram: parrifin (left) & laurlaursing (right)


I stopped Kelsie because I loved her lavender colored hair and overall ’90s pastel aesthetic, but I didn’t realize that she was also a fellow boutique owner until I looked up her Instagram and saw that she runs a rad shop called With Lavender and Lace. I love a hairstyle that’s also a smart branding decision!

Instagram: withlavandlace


When Alicia walked through the vendor tent, her energy and confidence just radiated through the whole space. I loved how she rocked this leather harness and floppy hat like a queen and a witch at the same time. I also wasn’t at all surprised to learn that Alicia was part of a post-punk band, Ganser.

Instagram: ganserband


I’ve known Morgan for a few years and I’ve always loved his personal style. I can always count on him to inspire me and give me ’90s fashion feels. This American flag tee paired with the skinny jeans and combat boots was everything I expected and wanted to see from Morgan at Pitchfork.

Instagram: mbwispower

Yours Truly

Representing for my big armed babes, I sported this super fitted bodysuit from Chicago-based brand Proud Mary Fashion with a rainbow fur fanny pack from my own line. Even through the heat, the rain, and the sheer exhaustion, I was still feeling myself.

Instagram: readytostare