all photos by jessie barber


best of #lollalook

see all of our favorite outfits from lollapalooza 2014!

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!

LollaLook Fashion Icon: Stella

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!"

LollaLook Fashion Icon: Miss Tosh

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."

LollaLook Fashion Icon: Taylor Les

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."

LollaLook Fashion Icon: Taryn Shultz

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."

LollaLook Fashion Icon: Melissa Gloodt

Key Outfit Piece: H&M necklace

What Jessie Loved Most: "Melissa’s necklace and boots combo"

LollaLook Fashion Icon: Fallon

Favorite Nylon Cover:

April 2013 cover with Hayley William


What Jessie Loved Most: "Fallon's mix of textures, including the lace bike shorts and the floral top."

LollaLook Fashion Icon: Erin Cullison

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."

LollaLook Fashion Icons: Hope Sorge (left) and Olivia Jones (right)

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.

LollaLook Fashion Icon: Kim

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!"

LollaLook Fashion Icon: Matthew

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!

LollaLook Fashion Icon: Allie Staples

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."

LollaLook Fashion Icon: Kate

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."

LollaLook Fashion Icon: Emily

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."

LollaLook Fashion Icon: Francesca Hidalgo

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!).

LollaLook Fashion Icon: Siena Reese

Key Outfit Piece: Vintage kimono

What Jessie Loved Most: "Siena was super cool. Her vintage kimono played nicely with her metallic crossbody."

LollaLook Fashion Icon: Megan

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!"

LollaLook Fashion Icon: Alex Maier (left) and Nina Jonnson (right)

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.

LollaLook Fashion Icon: Caitlin Pilgrim

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.