Summer Street Fest Style
Easy, Breezy Looks for Chicago’s Street Festivals

Even though the temperatures might still be a bit chilly, the Chicago cultural calendar tells us that summer is officially here! Fest 2

As Chicagoans, we spend much of the year shuttered inside to avoid the frighteningly freezing winter weather.  That’s why, when Spring hits, the city’s streets become our playground.

The ever-growing list of neighborhood street festivals are the perfect way to enjoy our fleeting warm weather.  And, they’re the perfect excuse to show off your favorite summer styles.  Read on for some fun inspiration for your outings to the best of Chicago’s street parties.

Light & Cool

Spending the day at a street festival is very cool, but it can also get very hot.  The sun beats down as
Fest 1you dance to great bands amidst a throng of fellow festival-goers.  If you’re not dressed for the heat, a fun day can turn swelteringly uncomfortable pretty quickly.  So, it’s crucial to pick the perfect outfit
that allows you to remain cool as a cucumber throughout the day.

We recommend sticking with breathable fabrics, like linen and lightweight cotton.  And choose light colors – they’re more summer-appropriate and won’t absorb the heat from the sun.  Though you might want to show off your toned summer physique, looser cuts will keep you cooler.  There’s a reason why those flowy, boho dresses are so popular at summer festivals.

That’s Your Bag

The bag that’s perfect for a formal night out is most definitely not the same bag you’ll want when you fest 4hit the summer street fests.  The key components of a good festival bag are size and accessibility.  First, make sure that it’s big enough to accommodate some necessary supplies (tissue, hand sanitizer, small bottle of sunscreen, etc.) but not so big that it’s annoying to hold all day.

Also, it’s key that you don’t actually have to hold onto the bag at all.  Cute clutches will become a nuisance, and shoulder bags easily slip off as you jostle through crowds or try to eat a gyro while holding a beer.  Cross body bags work best, especially ones that close securely.


While a funky pair of cowboy boots can look great with a summer sundress, they may not be the best choice for a street fest.  If you want to stay cool and be comfy, sandals are your fest 5friend.  But, be careful about rocking your favorite heels.  You’ll likely be standing for several hours, and the heels that felt fine when you put them on will probably become unbearable after 3 hours on your feet.

If you can’t give up heels entirely, then wedges are a good compromise.  You’ll be more solid and less likely to pack it in early because of sore feet.  It’s also a good idea to wear a pair that has a back-strap.  While walking through crowds, it’s pretty easy for someone to step on the back of a flip flop, causing you to lose a shoe.


Do not, we repeat, do not leave home without sunglasses when heading out to fest 6your local neighborhood fest.  Even if the day is a bit overcast when you leave, you never know when the sun will peak its head out and make you regret leaving your sunnies on the kitchen table.  They’ll allow you to look at the stage and food menus without squinting, and make you look a lot cooler.

While your daily look might be simple, understated black or tortoise shell frames, the summer fest is the perfect time to debut some frames that have a bit more personality.  Don’t be afraid to experiment with color, shape, size and fun embellishments.  But, you may want to come down and try them on in person – what you like online might not be a good fit for your face.

Whatever your summer style is, you can use these guidelines to help guide your festival fashion.  The main goal is to find the perfect intersection between comfort and style.

Throw on a breezy dress, your wildest sunglasses and get out in the sun to enjoy the glory of a Chicago summer while it lasts.  Happy street festing everyone!

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