Lollapalooza 2012: What to Wear

The best weekend of the year is FOUR days away. On Friday, Grant Park will be transformed into a giant music venue as fans and artists will fly in from all over the world for Lollapalooza. With over 160,000 people estimated to be in attendance, there are bound to be some serious people watching opportunities. As you’re creating your custom Lolla schedules and RSVP-ing to the best Lolla after-parties this week, we’re here to help make sure you also look your best this weekend both at the fest and at the after-parties (in case you run into Frank Ocean at Buckingham Fountain on Saturday night).


You really can’t go wrong with a classic pair of jean shorts for Lolla. Mine are a DIY pair I chopped off last week after I found Levis jeans for $2 at a local thrift store. To dress up the “jorts” look, tie up a classic blouse like the one above from J Crew and grab a fringe clutch. If shorts are not your thing, go with a cotton maxi skirt in a bright color, such as the one above from Old Navy. Play up opposites and couple your long skirt with a crop top from PacSun. The last two looks show off the color of the moment- mint. My new H&M mint shirt is fashionable and functional- the top incorporates the popular mesh trend seen all over designs these days, while the bottom of the shirt is made of cotton. I paired my Forever21 mint shorts, on the other hand, with one of the softest tanks own, the Madame tank from Sir and Madame. To finish off the look, add a bag – this purple suede shoulder bag from Top Shop was made to fit the essentials for any fest- phone, sunscreen and camera.


Vintage jerseys will never go out of style.  Jordan, Pippen, even Magic- the real Dream Team is always well received in Chicago. If you want to eliminate the “tank tan” though, go for a graphic t-shirt- the more unique the design on the shirt, the better. Michael coupled his Rocksmith T-shirt with tailored painters pants from Old Navy  and a baseball hat from Uprise. Linen is a good way to stay cool during Lollapalooza. For a twist on the classic white linen pants, choose linen shorts in a light yellow or mint and top it off the outfit with an airy button down like the one above from H&M. Long jeans for summer music festivals are never encouraged  unless they’re rolled up, like the pair above from Cheap Monday. Keep it simple on top with a plain tank from Top Man and this bracelet from Sir and Madame.

What Not to Wear

Lollapalooza is typically the hottest weekend of the year. Temperatures will likely be in the 90s, so layers (or winter coats) are not advised. Please also leave your Lebron James jerseys at home (or better yet do yourself a favor and just get rid of them for good). Trucker hats went out of style about a week after they were in style, and socks and sandals were never a trend.


Filed under Maggie, Style

6 responses to “Lollapalooza 2012: What to Wear

  1. anonymous

    That maxi skirt would be way too hot to wear to Lolla! Same with the long sleeve button-downs.

  2. Love Button

    I love that you mentioned crop tops in your suggestions for Lollapalooza 2012. It’s huge this summer. Check out my post on the trend:

  3. Bob

    Bob will be wearing cut off shorts and a wife beater

  4. maggie L

    Dang, now I.gotta go find a new outfit for lolla since my parka is apparently on the not to wear list…. :/

  5. Pingback: Lollapalooza 2013: What To Wear | acityinthemidwest

  6. Pingback: Lollapalooza 2013: What to Wear (Guys Edition) | acityinthemidwest

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