We love music festivals for two reasons: the music (obvi) and the festival fashion. This year, while team NYLON hung out in the Samsung Galaxy Lounge interviewing our favorite bands, we sent blogger Jessie Barber of Mini Penny to capture all of the best street style at Lollapalooza 2014. We also got some inside deets on each outfit, plus a fun fact about these fest fashion icons—including our #LollaLook winner, Caitlin Pilgrim! Flip through the gallery to see our favorites from the Grant Park party and stay tuned for our artist interviews on nylon.com!
best of #lollalook
see all of our favorite outfits from lollapalooza 2014!
all photos by jessie barber
Favorite NYLON Issues: Everything with Emma Watson
What Jessie Loved Most: “I bumped into Stella on the street and she was incredibly friendly. It was totally natural to photograph her because she had impeccable, effortless style. I love the details, from her belt to her boots!”
Key Outfit Piece: Miss Tosh is a designer, and is wearing her own pieces—so rad!
What Jessie Loved Most: “Miss Tosh really stood out among the crowd. Her whole look was complete, from head to toe, so I wasn’t surprised to find out that she had designed her own outfit.”
Key Outfit Piece: Necklace from Urban Outfitters and boots from a small store in Sedona, Arizona.
What Jessie Loved Most: “Taylor took this simple white tunic and accessorized it perfectly, making it an awesome festival look.”
Key Outfit Piece: A’Gaci shorts
What Jessie Loved Most: “Taryn had the layering game down. The subtle hint of her fun shorts through the sheer top caught my eye. She paired it with a great pair of boots for an edgier look.”
Key Outfit Piece: H&M necklace
What Jessie Loved Most: “Melissa’s necklace and boots combo”
Occupation: Works in fashion PR in NYC and loves NYLON!
What Jessie Loved Most: “It was instant love with Erin’s blush-colored palazzo pants, delicate jewelry, and perfect festival up-do.”
Most Excited to See: Chance The Rapper
What Jessie Loved Most: “These ladies managed to stay dry despite the downpour. Hope’s front-tie, side-split flannel looked great with her weather-appropriate sandals, while Olivia rocked festival classics like her hat and halter.
Key Outfit Piece: Chain headdress from Forever 21
What Jessie Loved Most: “Obviously, Kim had awesome accessories! She’s a fan of Vanessa Mooney but found this headpiece at Forever 21 and couldn’t pass it up!”
Self-proclaimed Style: Subtle Patriotic
What Jessie Loved Most: “I spotted Matt coming out of the VIP area. As far as mens fashion at the festival, he was in his own league—killing it with those overalls!
Most Excited to See: Skrillex
What Jessie Loved Most: “Allie was great! Her hat caught my eye from across Buckingham Fountain. It had a great silhouette.”
Key Outfit Piece: Vintage Valentino duster (brave considering the weather!)
What Jessie Loved Most: “Kate’s outfit was one of my favorites of the entire weekend. She found the hat just before I snapped the photo. Her boots were rugged, her accessories grand, and her vintage Valentino duster sealed the deal.”
Most Excited to See: Chromeo
What Jessie Loved Most: “Emily was the first person, aside from myself, that I actually saw in rain boots. It rained on and off the entire third day of Lollapalooza, and I totally appreciated that she paired these up with her floral dress.”
Most Excited to See: Chromeo
What Jessie Loved Most: “Francesca pulled off the high-waisted-slash-crop-top look the right way! That jacket tied around the waist, matched up with her rainboots made it obvious this wasn’t her first rodeo (err, festival!).
Key Outfit Piece: Vintage kimono
What Jessie Loved Most: “Siena was super cool. Her vintage kimono played nicely with her metallic crossbody.”
Key Outfit Piece: A convertible dress from a reggae festival she purchased a few years ago.
What Jessie Loved Most: “I loved that Megan had a different look than a lot of other festival-goers. These boots were such a good direction to go with that dress!”
Best Duo Look: These two spent the day shooting outfits at the festival together
What Jessie Loved Most: “These two were just really awesome. They were absolutely the ‘cool’ couple—subtly matched, with details like the leather camera strap and rain gear.
Key Outfit Piece: Lovely layers
Why Caitlin Won Our #LollaLooks Contest: Caitlin follows tons of fashion brands on social media, which is how she found out about our contest, so she’s getting awesome inspo from all the right places. Mix that with her own personal style—casual and unpretentious—we knew she’d be the perfect winner.