Even if you can’t stand weaving through that bottleneck of people that always occurs around the food, you can’t miss out on going to the Wells Street Art Festival. Not to be confused with the Old Town Art Fair (which is held the same weekend further north, winding around the side streets in Old Town), the Wells Street Art Festival is more of a block party with thousands of your closest friends. Don’t get me wrong, there’s certainly a lot of art to see. But it’s also the place to be seen this weekend whether you’re just hanging out with friends at the festival, or you’re lucky enough to live or know someone who lives in the area, so you can spy on the action below from a balcony or deck. If you’ve never gone before, with all the boutiques, stores, restaurants and bars flanking the festival on each side of Wells St., it certainly is an event to behold in Chicago. If you have been before, you know what I’m talking about, and you know that you can’t just show up to a scene unprepared wardrobe-wise. So let’s get you an outfit, girl!
Okay, so I always tend to lean toward dresses for these types of events because a) they’re easy and b) they’re your best bet if you don’t want to be too warm or too cold as you can always layer or un-layer if need be. These lightweight drop waist dresses are in right now and perfect if the weather is a little cooler and not suitable for something sleeveless. This one is in black but they also are easy to find in denim or khaki. I love this purple feather printed tunic as it’s perfect to wear alone or with leggings underneath. For a warmer day (or if you’re just going to brave it no matter what the temperature), try this braided one shoulder dress which can easily take you from day to night, should you have the stamina to continue the festivities into the wee hours.
If you’re not a dress girl, rompers will offer you a trendy alternative this season. Here’s a comfy racerback capri length jumper (rompers are have a short bottom, jumpers have a pant bottom) that you can easily accessorize with a trendy belt, long necklaces and cute shoes. This deep-v black one by Twelfth St. by Cynthia Vincent is also versatile, but for more romper picks, check out my lookbook.
You can never go wrong with good ‘ol shorts and jeans. How cute would this fun tunic be with these striped boyfriend shorts, or this floral embroidered peasant top with white denim capris?
Here’s an example of one of the dresses from above with cute shoes, and a cute bag:
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