POPSUGAR Fashion

How Chic-ago! The Best Festival Looks From Lollapalooza

Aug 4 2014 - 12:45pm

Capping off the weekend with a little rain and a lot of mud, Lollapalooza has officially come to a close. While most music festivals — Coachella, Bonnaroo, and Glastonbury [1] — put up concertgoers in remote areas like the desert or a farm, Chicago's band-filled weekend [2] was as urban as it got. Nestled in the heart of downtown, it offered up a true mix of style, from flower crowns and cutoffs to black leather jackets and motorcycle boots.

We searched every corner of Grant Park for that quintessential festivalgoer uniform — along with other Summer fashion inspiration. We've found some serious Coachella competitors, wearing everything from breezy linen jumpsuits and statement-making sheer tops to vintage YSL sunglasses and bold leather backpacks. See the fest's best looks, and check out the most memorable moments [3] from the entire Lollapalooza weekend!

Lollapalooza 2014

When crop tops are everywhere, it was refreshing to see this bare midriff in a different style. Lauren's knot-tied maxi dress was one of our favorites – as was the way she added a mismatched Topshop [4] necklace and sporty Oakley [5] shades.

Lollapalooza 2014

Dare to dress like you did in junior high! Lydia went with a vintage-like D.A.R.E. tee, some acid-wash overalls and a black leather fanny pack to bring a little nostalgia to Lollapalooza.

Lollapalooza 2014

Umbrellas only get you so far at a festival. Abby opted for a sturdy Forever 21 [6] hat that complimented her vintage denim shirt.

Lollapalooza 2014

If you're going to wear shorts, try more feminine styles, like Jen's Free People [7] playsuit – cinched with a cute white lace cardigan – and Sarah's BCBG crochet shorts with scallop trim.

Lollapalooza 2014

Rain didn't stop Abby from wearing her beaded floral Topshop [8] dress.

Lollapalooza 2014

Gabriella didn't mess around when it came to footwear. Her extreme gladiator sandals elongated her legs and somehow didn't compete with her printed Intermix [9] shorts or fringed Zara [10] top.

Lollapalooza 2014

Christina was all about her denim vest, which she paired with a Topshop [11] crop top and Jeffrey Campbell [12] flatforms.

Lollapalooza 2014

Show your spots with an oversized pair of MinkPink [13] sunglasses.

Lollapalooza 2014

If you have your own sense of style, don't change it just for the festival. Lydia stayed true to her retro sensibilities in a flirty dress and bold burgundy hat.

Lollapalooza 2014

White and gold played nicely together in this statement necklace.

Lollapalooza 2014

Heighlen loved how her extra-long Topshop [14] maxi skirt made sitting in the grass a breeze at the festival.

Lollapalooza 2014

What's better than a Velcro'd pair of old-school Tevas? DIY-studded Tevas.

Lollapalooza 2014

Whoever said preppy style has no place at a serious music festival hasn't seen this Tory Burch [15] flower wrap bracelet.

Lollapalooza 2014

Anyone who will wear oversized white shorts on the rainiest day of the festival isn't going to let anything stop her from having a good time. Yet, somehow Jenna made sure to keep her striped ASOS [16] top and shorts mud-free. The only victim? Her ASOS sandals.

Lollapalooza 2014

One of the rare Chanel sightings at Lollapalooza was this black quilted backpack.

Lollapalooza 2014

Tedi looked beyond comfortable in this Free People [17] t-shirt and Anthropologie [18] maxi skirt.

Lollapalooza 2014

There's no such thing as too many accessories, as Tedi pointed out with her mirrored Ray-Bans, a braided Free People [19] headband and Kendra Scott [20] earrings.

Lollapalooza 2014

Bringing a '90s vibe to Lollapalooza, Monique wore a sheer Lush shawl over a lace-trimmed Urban Outfitters [21] top and, naturally, vintage Levi's. Her cutout Jeffrey Campbell [22] boots offered up added edge.

Lollapalooza 2014

Wearing your favorite pair of sunglasses? Just secure them with a colorful beaded chain from Bijoux Beautique [23].

Lollapalooza 2014

Like friendship bracelets, this pair showed their love in two different colors of the same Free People [24] dress. Jenna played up the cream dress with colored Ray-Bans, and pal Nicolina chose an Aldo bag and Target boots.

Lollapalooza 2014

Sometimes, two bags are better than one. Marissa paired her black purse with a vintage Caiul camera case.

Lollapalooza 2014

When you've got a jumpsuit, from Reformation, that makes this stylish of a showing, go neutral with accessories, like Katie did with her vintage beach bag, Toms sunglasses and shoes, and Bones & Feathers jewelry.

Lollapalooza 2014

One of Summer's hottest sunglasses trends? Circle rims, similar to this Toms pair.

Lollapalooza 2014

It's no surprise Christina Pacelli's day job is as a fashion stylist. The street style pro, in an Alexander Wang [25] leather shirt and Alaïa skirt, accessorized with a 3.1 Phillip Lim bag, Celine shades, and mint green Topshop [26] shoes.

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The edgiest statement necklace of the weekend was actually two well-stacked pieces.

Lollapalooza 2014

Who needs an arm party when you've got this? Although we at first couldn't get enough of this Rue Gembon palm cuff, we soon became obsessed with the Lady Grey [27] rings and Bing Bang bracelets.

Lollapalooza 2014

These chunky mint green Topshop [28] sandals might just be grass-stain proof!

Lollapalooza 2014

Want that just-rolled-out-of-bed look? Carly took it literally when wearing this adorable romper from Anthropologie [29], which was actually sold as pajamas. A vintage Louis Vuitton [30] crossbody and Old Navy [31] sandals completed the look.

Lollapalooza 2014

Southwestern-inspired carryalls, like this multi-colored woven backpack, were all over the festival grounds.

Lollapalooza 2014

We thought Emily's crop top styling was so refreshing. Instead of pairing her formfitting halter crop top with equally tight shorts, she played with proportions with a pair of super-wide-leg pants.

Lollapalooza 2014

Feathers, a few beads, and a leather strip are all that it took to craft these DIY [32] earrings.

Lollapalooza 2014

The perfect dress to take you from Lollapalooza to dinner in the city? This coral-and-black striped one. Of course, we appreciate how Darcy dressed it down with a cool pair of combat boots.

Lollapalooza 2014

If you aren't going to wear sneakers on your feet, why not put some lace-ups right on your satchel?

Lollapalooza 2014

White on white! Caitlin paired a Nasty Gal [33] dress – over a black Urban Outfitters [34] bralette – with a Steve Madden [35] crossbody bag.

Lollapalooza 2014

A basic white leather Steve Madden [36] mini-bag gets an edgy upgrade with three-zipper detailing and a chain-link strap.

Lollapalooza 2014

Perhaps our favorite strapless top of the fest, Mary's aquamarine pleated sweetheart top looked beyond comfortable.

Lollapalooza 2014

This concertgoer loves public school boys, and clearly the J.Crew x Public School collaboration where this graphic tee came from.

Lollapalooza 2014

It's a daring fashion lover who brings this gorgeous 3.1 Phillip Lim bag through the paces of a sold-out music festival.

Lollapalooza 2014

Whitney was a vision of relaxed comfort in loose Oneil tank, Chan Luu [37] wrap bracelets, and Toms shades.

Lollapalooza 2014

We were so excited to hear these cute two-tone sandals were made by Toms.

Lollapalooza 2014

Andie channeled the '70s with her flared pants and fringe-hemmed tank, both vintage.

Lollapalooza 2014

A cool styling trick that also helps avoid mud splatter after a momentary festival rainstorm? Knotting the hem of your dress, like Rosemary did.

Lollapalooza 2014

This vintage beaded crossbody bag looked as sweet as candy.

Lollapalooza 2014

Shorts chic! Melodey opted for bold red Charlotte Russe [38] shorts, while Maggie, in a comfy Ralph Lauren [39] top and Toms, chose a striped J.Crew pair.

Lollapalooza 2014

A woven purse that might be meant for more sophisticated settings can still play well at a muddy music festival.

Lollapalooza 2014

Not a hat we typically spot at an outdoor Summer music festival, but we still adored Ronna's vintage headgear.

Lollapalooza 2014

A look cool enough for the hottest day was found on Stephanie, in crisp Joe's Jeans shorts and a white Vince top.

Lollapalooza 2014

While backpacks are ubiquitous with Lollapalooza, we swooned over this luxe leather MCM [40] bag.

Lollapalooza 2014

Sure, it might not be the easiest outfit when in line for the bathrooms, but how could Molly not wear this gorgeous Anthropologie [41] jumpsuit? Pairing the piece with a Forever 21 [42] shawl and fringed crossbody bag, she looked perfectly at ease.

Lollapalooza 2014

Tricia was flirty in florals in a Bebe dress and an Urban Outfitters [43] black bucket bag.

Lollapalooza 2014

These heart-painted Toms brought the love to Lollapalooza.

Lollapalooza 2014

We thought Olivia's vintage embellished tank top — with Rag & Bone booties — was sheer perfection.

Lollapalooza 2014

The urban setting of Lollapalooza makes this decidedly urban look fit right in with the flower crowns and cutoffs. Acacia suited up in an all-black ensemble that included an ASOS [44] leather jacket, American Apparel jeans, and Urban boots.

Lollapalooza 2014

Perhaps the most fitting jacket of the festival, this hand-painted "Music Is the Answer" army jacket, which was designed by Jac Vanek, said it all.

Lollapalooza 2014

A music-fest style philosophy to live by? You can't go wrong in denim cutoffs! Flora paired hers with a floral Urban Outfitters [45] top and suede fringe sandals.

Lollapalooza 2014

It doesn't get more all-American than with Kelly's PacSun sleeveless button-down and cuffed Sanctuary shorts. Sophia — although not rocking the red, white, and blue — had an equally fun vibe in a Forever 21 [46] romper.

Lollapalooza 2014

Cristin went full-on boho with her Jen's Pirate Booty dress and a turquoise Alyse Ziede statement necklace.

Lollapalooza 2014

A true festival veteran, Alexa was prepared for any type of weather with her teal Roberto Robledo jacket and Pony high-tops.

Lollapalooza 2014

Small necklace — big statement. We got an up-close look at this gold Freedom handcuff accessory.

Lollapalooza 2014

The halter neckline of Marie's H&M [47] crop top has been on many red carpets this season, and we love how she paired it with a black-and-white printed Kohl's maxi skirt.

Lollapalooza 2014

Besides embracing the requisite floral crown, Yasmine got into the festival spirit in a revealing fringe top and vintage YSL sunglasses.

Lollapalooza 2014

With so many loose floral dresses at Lollapalooza this year, Katy set hers apart with a flouncy Forever 21 [48] hat and a slouchy H&M [49] bag.

Lollapalooza 2014

One of the more girlie looks came from Katie, in a white chiffon skirt with a matching fedora.

Lollapalooza 2014

Crop that top! Kendra wore a fitted American Apparel crop top over her Skylark pants, while her well-coordinated pal Jac wore hers with a sheer black Urban Outfitters [50] skirt and a leather jacket.

Lollapalooza 2014

When you opt for a monochromatic outfit, why not pile on the jewelry? These layers of silver necklaces from Aldo added an edgy vibe to a basic black top.

Lollapalooza 2014

If you want a look with coverage that's still supersexy, try Cristina's sheer floral Nasty Gal [51] top, which she paired with black Urban Outfitters [52] shorts and a Coach crossbody minibag.

Lollapalooza 2014

If you are going to wear sneakers, might we suggest these gold Reeboks with multicolored pink laces?

Lollapalooza 2014

Neutrals were a smart move for these friends when it comes to effortless looks that transition from the festival to the city. They had the minimalist look down, from Amy's checked H&M [53] shawl to Melissa's J.Crew dress to Alannah's black Gap jeans (with a pop of color with mirrored blue Ray-Bans).

Lollapalooza 2014

Overalls made a big comeback on the festival circuit, and Lauren's American Eagle [54] ones were the perfect mix of comfort and style — as were her accessories, a Rebecca Minkoff [55] bag and studded Frye [56] boots.

Lollapalooza 2014

While some opt for loose-fitting clothes for a full day at the festival, Ange brought her A game in a body-con dress but dressed it down with a flannel shirt and fringe boots.

Lollapalooza 2014

Leather and chains were the key materials in this sandals. Paired with a beaded ankle bracelet, they looked both edgy and girly.


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