9 Ways To Survive The Windy City In Summer

by Charmaine Simmons

Summer is readily approaching and that means one thing: It's time to plan our summer trips. And that includes a vacation to Chicago. Wait, what? Chicago? Just hear me out!

Most of us have been Pinning the most dreamy, wanderlust-inducing photos onto our boards of holiday getaways. And while some are envisioning themselves on a beach vacay, some of us can only afford visiting cities within the United States. Instead of the super trendy Los Angeles or Miami, why not plan a trip to Chicago? Chicago is one of the best cities in the country (well, at least in the Midwest)! And although I am a little bias because I was born and raised here, I think it's pretty true. Chicago, or The Windy City, has so many fun activities and hidden gem attractions that tourists can visit and fall in love with.

As adults, we have (hopefully) figured out how to optimize most of our luggage space, but Chicago weather can make this an even more difficult task. Chicago weather is just so unpredictable, and the city is notorious for having a gloomy, rainy 60-degree day only to be followed by a sunny, solid 80 degrees the following morning.

Remaining fashionable while being weather conscious is one of a Chicagoan's worst struggles. It's cool in the morning, warm in the afternoon, and cool again in the evening in this windy city. Thus, staying stylish in Chicago can be tricky — but it can be done.

Here's a style guide on packing for Chicago's wacky, summer weather to ensure you will be one of the most fashionable tourists strolling the streets.

1. Trench Coat

Belted Crepe Trench Coat, $48,

Remember when I mentioned the random rainy days in Chicago? I wasn't kidding. Pack a lightweight trench coat that will not take up too much space in your luggage. It will keep you dry while looking quite chic in the rain, while exploring the city.

2. Fun Slip-On Sneakers

Sam Edelman's Becker Calf-Hair Slip-On Sneaker, $62,

Slip-on sneakers are perfect for your trip to Chicago and beyond. Ideal for those long strolls down Magnificent Mile and for those random train rides on the Red or Blue Line. Plus, these shoes add a punch of edge to the simple color palette that most of us pack while traveling.

3. Distressed Boyfriend Jeans

1969 Distressed Authentic Boyfriend Jeans, $80,

Speaking for myself, I am not a lover of tight-fitting jeans, especially in the summer. I suggest bringing a pair of boyfriend jeans instead of skinny jeans — because boyfriend jeans are like wearing fashionable sweatpants outside.

You will not regret wearing boyfriend jeans on a day out at Navy Pier or grabbing ice cream at Jeni's in Wicker Park. Plus, boyfriend jeans will look great with the fun slip-on sneakers that I listed above.

4. Gladiator Flat Sandals

Strap Cord Sandals, $40,

Are you a gladiator (that was a Scandal pun)? But really, Chicago does have amazing summer weather at times, too. These gladiator sandals are perfect for cute, simple lunch dates in Lincoln Park. Or, you can just wear these sandals anywhere because they are so chic. The choice is yours, darling.

5. Pleated Sundress

Strappy-Back Pleated Dress, $15,

"What to wear with the gladiator sandals," you asked? This high square neckline dress will pair well with the sandals or, perhaps, the slip-on sneakers as well. This red pleated dress is perfect for any daytime activity.

6. Denim Shirt

Women Denim Cropped Long Sleeved Shirt, $13,

This denim shirt has long sleeves that are great for those chilly evenings in Chicago when the temperature drops. This means that you will not be freezing while grabbing dinner at a restaurant near Lake Michigan. Plus, denim shirts can be paired with almost anything that you packed.

7. Floppy Hat

Wool Floppy Hat, $18,

Big, floppy hats are not just for Southern derby days or Pharrell. No matter if it is a rainy, gloomy day or if it is sunny and warm, this hat will help you throughout your Chicago trip. Also, it will have you looking quite cool while doing so.

8. Heeled Sandals

Knotted High-Heel Sandals, $60,

Planned a night out to see a play at Goodman theatre? Maybe a sexy, date night with your significant other or a fun night out at a bar in the South Loop? No matter which question you answered yes to, these heeled sandals will work with any event above. Plus, it's always fun to play dress up every once in a while.

9. Baseball Jersey

Chicago Cubs Women's Cool Base Jersey by Majestic Athletic, $70,

I mean, how can you visit Chicago without attending a baseball game? Pretend to be a Cubs fan (or you can really be a Cubs fan) and wear their jersey to a Cubs game at Wrigley Field. You will definitely will look like a typical Chicagoan by wearing this jersey while eating a Chicago-style hot dog and drinking beer.

Images: Fotolia; Courtesy Brands