1. Stylemax

Launched in 2000, the largest apparel and accessories trade show in the Midwest takes place four times a year at the Merchandise Mart. On the show floor, buyers can learn about trends in categories from footwear to accessories and premium denim. Ancillary events include cocktail parties and networking lunches. Next: October 27-29, 2019
Photo: Barry Brecheisen
2. Children's Service Board of Lurie Children's Hospital's Gold Coast Fashion Awards Show

The Children’s Service Board’s signature fund-raising event took in more than $1 million this year. Held at Revel Fulton Market, the event included a cocktail reception with snacks from several local restaurants. The fashion show displayed styles from Neiman Marcus Michigan Avenue and was capped off with a paddle raise and live auction. Next: Fall 2020
Photo: Sean Su/Purple Photo Co
3. The School of the Art Institute of Chicago Fashion Show

For more than 85 years, the school’s fashion design department has hosted an event each spring to showcase its students’ collections. This year, the runway show and exhibition had a dystopian theme and featured more than 260 looks from 125 students. About 500 guests attended the event. Next: May 1, 2020
Photo: James Prinz Photography
4. St. Jude's Dream a Little Dream Luncheon and Fashion Show

This stylish event, held at the Donald E. Stephens Convention Center, offers a fashion show and raffle prizes, along with an inspiring speaking program. In 2018, the event drew 1,150 guests and raised $418,000. This year, the show celebrates its 25th anniversary. Next: November 10, 2019
Photo: Courtesy of St. Jude
5. Driehaus Awards for Fashion Excellence

Themed “Infinite Possibilities,” the event kicked off with a cocktail reception and segued into a runway show competition with designs from 24 local fashion students. The winner received a prize package that included a display at Neiman Marcus Michigan Avenue. The event raised more than $140,000 and drew 300 guests. Next: Spring 2020
Photo: Kasia Jarosz