2nd Annual Chicago Fashion Week

I wouldn’t consider myself a fashion expert by any means. However, I would describe myself as a lover of fashion. I remember heading to the library in high school and college to scan through all the fashion magazines and then try to recreate the looks on the cheap. (I still pretty much do the same thing now, except I scour online websites).

I was sooooo excited to attend the inaugural Chicago Fashion week in 2024. The runway show I attended at the Chicago Cultural Center was top notch. (See here).

This year Chicago outdid itself again! The 11-day citywide celebration of Chicago’s vibrant fashion community takes place across the city as part of its second edition, October 9 – 19. The event calendar includes more than 50 fashion shows and presentations, panel discussions, retail marketplaces, educational programs and more in partnership with local fashion organizations, retailers and fashion designers.

“The second edition of Chicago Fashion Week is a testament to the creativity and collaboration that thrive in Chicago,” said John Leydon, founder of Chicago Fashion Week.

Chicago Fashion Week offers a variety of public events in six categories, including fashion education, fashion exhibition, in-store events, retail markets, runway fashion events and social fashion events. All events are open to the public, many free of charge with advance registration.

I was lucky to attend as media and cover the following events:

VIP Chicago Fashion Week Launch Party
City of Confidence Fashion Experience

Check out all the FUN I had below and if you want to attend Chicago Fashion week, check out the schedule of events at Chicagofashioweek.com.

Chicago Fashion Week 2025 VIP Launch Party

An invitation-only celebration of Chicago Fashion Week’s community of designers, photographers, models, retailers, event organizers and supporters.

City of Confidence Fashion Experience

Step into a world where style meets empowerment at the City of Confidence Fashion Show, presented by Confidence Apparel during Chicago Fashion Week at Navy Pier. This immersive, high-energy experience transforms the former Illuminarium space into a modern luxe runway showcasing bold streetwear, cutting-edge designs, and inspiring stories. Featuring live music, VIP lounges, fragrance bars, interactive activations, and a celebration of individuality, the event promises an unforgettable multi-sensory journey. With the Chicago skyline as its backdrop, City of Confidence is more than a fashion show—it’s a statement of power, passion, and purpose.

The City of Confidence Fashion Show by Confidence Apparel is a premier event of Chicago Fashion Week 2025, hosted at Navy Pier — in exclusive partnership with Navy Pier.

This collaboration between Confidence Apparel and one of Chicago’s most iconic landmarks, Navy Pier, makes this an unparalleled experience backed by a premier partner. The high-energy, fully immersive evening showcased modern luxe streetwear, interactive activations, and bold creative expression, setting a new standard for Chicago Fashion Week.

Produced by ZZAZZ Productions and hosted by Val Warner (ABC Chicago) with Sydney Supple on the red carpet, the immersive show blended modern luxe street style with artistry and philanthropy. Guests enjoyed:

A dynamic runway presentation featuring exclusive Confidence Apparel designs.
Special musical performance by Chicago’s Own AGT 2025 finalist, Leo High School Choir.
The Pink Runway Tribute honoring breast cancer survivors, with a portion of ticket sales supporting A Silver Lining Foundation.
Val Warner of ABC Chicago as the evening emcee.
Sydney Supple hosting the official red carpet arrivals, interviewing designers, models, and VIP guests.
Live art painting by renowned artist Kudzai Mutasa, culminating in an exclusive auction to close the night.

VIP & Media Lounge — Chef Art Smith’s Reunion Patio

An elevated pre-show experience featured:

Chef-curated tastings by Chef Art Smith.
Sparkling pours from LaMarca Prosecco and wine pairings by White Haven Wines.
Creative wellness drinks from Vitamin Water.
Glam touchups at the Lamik Beauty VIP Glam Bar.
Exclusive fragrance bar sampling.
VIP guests contributing the first brushstrokes to Kudzai Mutasa’s live art piece before it moves outside for completion.