You wouldn’t know it from the dreary late spring weather we’ve had lately, but summer is indeed around the corner. Along with rising temperatures, plants budding (finally!) and longer days, the May-June is officially the beginning of Chicago’s much anticipated festival season. Anyone who’s hibernated through the winter knows they will be rewarded come summer in the form of a plethora of outdoor street festivals. Summer in Chicago means you never have to look far for fun weekend events. Each street fest has a unique feel and crowd to match, making every weekend a chance to evolve your interests – and look. Exploring different festivals means venturing into new neighborhoods, each with its own distinct style. Read on for a few of my favorites and the styles you can expect to see.
Old Town Art Fair: Saturday June 13 – Sunday June 14
There are plenty of art and craft festivals throughout the summer, but this is one of the larger ones. Wells Street in Old Town is the perfect setting for this fest. During the day you can leisurely peruse local artists’ booths and pick up some one of a kind touches for your place. On a perfect, sunny day walking through the tents with a lemonade in hand you feel as though you just came from lakeside picnic, but impeccably dressed of course. The evening takes a turn to a faster pace so you want to make sure your outfit can transition from day to night easily. A swingy midi skirt and bright crop top fit the bill.
Taste of Randolph: Friday June 19 – Sunday June 21
While every festival has its fair share of fest food (read: fried, greasy, not ok for your beach body) it’s worth using your calories more wisely. We all know reservations at the restaurants on Randolph are hard to come by. Enter Taste of Randolph. Swing by this fest and try samplings from some of the most talked about eateries in town. Since you’re still on Randolph Street after all, you’re going to want to dress like it, but make sure you’re prepared for lots of standing and walking. You’re going to want to enjoy the tantalizing bites, fresh air and good tunes, so stylish comfort is key. Perhaps try out the newest silhouette of the season: Culottes.
Wicker Park Fest: Saturday July 25 – Sunday July 26
I might be partial since this is one of the best fests in my own neighborhood of Wicker Park, but it’s some of the best people watching you’ll do all summer. Wicker Park/Bucktown is home to the trendy hipster. Long seen as the “edgy” neighborhood in Chicago, it’s not uncommon to see skinny jeans, multicolor hair, tattoos and almost every guy sporting facial hair. This fest is almost like a mini-Lollapalooza, meaning you’re going to see a lot of boho chic ensembles. A breezy maxi skirt, crop top and gladiator sandals will keep you comfy and stylish in the heat.
Windy City Wine Festival: Friday September 11 – Saturday September 12
What could be better than sampling wines from around the world while taking in Chicago’s amazing skyline and lakefront? Not much. This festival takes place by the landmark Buckingham Fountain, which draws tourists and locals alike for a perfect photo-op so don’t let the fountain outshine your outfit. Since you’ll be downtown and sipping wine, your look should be classic. Think Parisian chic – effortless, downtown cool. A floppy wide brim hat and chunky heels make the work look all the way through sunset. Who knows where the night may take you?