What to Wear to Chicago’s Summer Festivals

Garnet Hill Dress c/o / Converse “Shoreline” Sneakers c/o Kicks USA / Kate Spade Bracelet (Old, similar here) / Vera Bradley Backpack c/o / Uniqlo Sunglasses c/o / Moon and Lola Earrings c/o Tuckernuck

Summer in Chicago is the best, and the city’s festivals and street fairs can’t be beat. Recently, Mitch and I have fallen into the wonderful habit of hitting up as many of ’em as possible on the weekends, and it’s been so much fun! Yesterday, we attended Ribfest (as amazing as it sounds) and Midsommarfest. We also may have spent way too long at HopLeaf, downing the establishment’s famous mussels and frites. ;) Today, we’re going to the Old Town Art Fair, which Mitch attended several times as a kid while growing up in Lincoln Park. (Happy memories!)

Attire for Chicago’s summer festivals is super casual: shorts, t-shirts, sundresses, flip-flops and sneakers. Because I have such fair skin, I’ve been opting for three-quarter-length t-shirt dresses. (This one from Garnet Hill is my fave! It has pockets!) This Vera Bradley leather backpack is a must-have as well, as it allows me to carry my heavy camera without killing my shoulder. (The one downside that comes along with having a full-frame.)

I should also mention my new sneakers! I had a pair of pink Converse high-tops in elementary school, and my mom was a huge fan of Converse when she was growing up. And while my friends have been all about the brand’s comeback in the preppy world for years now, I’d always been hesitant of jumping on board. (I think I was scarred from an unfortunate incident with Jack Purcells. Clown feet!)

But when Kicks USA sent me a pair of the Shorelines, I instantly fell in love. They’re far more feminine and smaller-looking than the original version, and they take very little time to wear in. They also go with a lot. They’re easily paired with t-shirt dresses, jeans and shorts–and they’re perfect for Chicago’s festivals and street fairs. :)

Sizing advice: Go down a half size. I typically wear a size 7.5, and went with a 7 in these.

Hope everyone is having a great weekend!