What is Chicago style known for? For this special collaboration, Gwynnie Bee asked me to describe the fashion scene in Chicago and choose 3 outfits to bring it to life! As y’all know – I’m from Alabama, but Chicago is my adopted city. I’ve lived here for over a decade and in that time, I’ve come to love Chicago’s bold, colorful and practical style. See what outfits from my Gwynnie Bee Closet I chose to represent my city’s fashion sense! AND BONUS INFO ABOUT GWYNNIE BEE’S SUMMER ROAD TRIP CONTEST!

*This post is sponsored by Gwynnie Bee and contains affiliate links. All opinions are my own. Photo credit for this post goes to Mindy Scott Evans of @mindycityy.

Chicago Style is Bold and Colorful

Chicago has a bold and colorful history and that is definitely reflected in many of the sartorial choices of its residents! When I think of the city, I think of strong design, balanced architecture, and bold choices. For my first outfit, I decided on this color-blocked shirtdress from eShakti.

The color is fabulous and deep – and the color blocking at the shoulders and hem give it a presence that is hard to ignore, even though it’s not “showy.” It’s a strong silhouette – and above all, it’s practical. It’s easy to wear, washable and you can move in it. Which absolutely defines Chicago Style!

Chicago Style Also Has Retro Vibes

Chicago fashion also has some flirty retro vibes, which is perfect for my love of pinup-girl fashion. This Cherry Velvet lemon print dress is simple, bright and fun.

After months spent cocooned away in big puffy coats, Chicagoans love to emerge from the winter in colorful, bright styles! This dress just screams Chicago summer to me!

Above All, Chicago Style is Practical

Even though Chicago is a major metropolis, it is firmly grounded in its Midwestern roots. And that means practicality wins the day with fashion. For a night out, you’ll find most Chicagoans in nice jeans and a colorful top and shoes you can walk in! That Midwestern sensibility inspired this look. The top is Kensie, and I simply love the floral print and asymmetrical design with ties at one shoulder!

Gwynnie Bee’s Summer Road Trip Contest Details!

This summer, Gwynnie Bee is gifting a #GBMyCityStyle Summer Road Trip Package for an amazing summer road trip valued at over $3,000! If you win, you’ll get to experience a new city and see first hand what style the city is known for!

The Grand Prize includes:

$1,000 Visa gift card for car rental, dining, and road trip snacks and souvenirs

$1,000 Hilton gift card

$600 in gas (Shell gift card)

$400 to Calpak for new luggage

1 year subscription to Gwynnie Bee (2-item plan)

To ENTER, all you have to do to enter is:

1. Share a photo on Instagram, Facebook, or Twitter, showing what you think your state, city/town, or area is best known for from a fashion perspective.
2. In the caption, say where you’re from and why the item or photo showcases your city’s style!
3. Tag! In addition to using #GBMyCityStyle in the caption, you must tag the official business profile of Gwynnie Bee on the site from which you’re entering (@gwynniebee).

Note: The social media profile from which you publish must be public so the GB team can see and accept your entry. You can also submit an entry using the sweepstakes form on this page. Entries not complying with all requirements will be not be accepted. You may enter once per day, now through 6/30/18 at 11:59 pm ET.