Your Style Guide To Chicago, Just In Time For Lollapalooza 2014!

Planning to go to Lollapalooza this year? Lucky for you, you have front row access to a real Chicago resident – that would be me –  who can be your sartorial guide to The Windy City (which just so happens to be the home of the annual music fest as it takes place August 1st – 3rd in Grant Park).
Now first things first I’m the realest, the weather in Chicago is unpredictable at best, seriously frustrating at worst. With that in mind, consider bringing a jacket along for the ride. Even in early August, a temperature drop is not out of the question – my tip? Use it to your advantage. After all, what could be more festival fabulous than a great beat-up leather or denim jacket?
With that being said, if you forget to pack a second layer (or ya know, a flower crown) you’re in luck – there happens to be plenty of amazing shopping in the city. If you plan on coming down for a few extra days (and you totally should!), here’s where to shop it, Chicago style.
While Michigan Avenue is Chicago’s most iconic stretch of retail, it isn’t a complete representation of what the city has to offer. Treat yourself to something that was made in Chicago (or at least sold at a boutique that was made in Chicago) by stepping off the beaten path and onto a more original one. Stick around Michigan Ave if you’re in search of all your trusty favorites (think Nordstrom, Zara, Forever 21, H&M, Bloomingdales) but venture to Oak Street if you’re looking for something totally high-end. The street, located in the Gold Coast, is home to Prada, BCBG and Kate Spade, among many others. Wicker Park is where you’ll find a healthy mix of Chicago-only boutiques and retail chains you know and love and Lincoln Park has a similar feel.
Heading to the city a few days early? Be sure to catch the July 26 and 27 installment of the Randolph Street Market It’s a full-on indoor/outdoor market where you can find tons of unique gems. Other boutiques Chicagoans love include Sofia and Edith Hart. For a pair of made-in-Chicago jeans (or more seasonally-appropriate denim shorts) be sure to check out Henry & Belle.
If you need a quick midday refresher, Elizabeth Arden’s Red Door Spa will be holding a Lollapalooza pop up salon right by the festivities. You can choose from a variety of on-the-spot treatments – think a quick makeup refresher, hair tinsel/feather application or a ponytail/braid/bun bar –  to pump your festival look up a few notches. The pop-up will be open from July 28 to August 3 with two extra days on July 24 and 25 and services are as low as $10.
As for where to spend your days when you’re not fist pumping and crowd surfing – hit the Gilt City Chicago ‘Better than Backstage’ party. Tickets are on sale now and aren’t cheap – but I can assure, this is the most stylish party in town. Spoiler alert: You may catch a celeb or two.
[Lead image via Theo Wargo / Staff / Getty Images]

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