From citywide cultural events like the 54th annual Chicago Pride Parade on June 29 to Millennium Park’s free summer concerts and film series spread from June to August, local and visitor fashionistas have a packed summer to show up and show out in Chicago.
Touching a range of tastes and styles — whether you’re hoping to immerse yourself in global fashion traditions, laugh through a themed comedy show or walk the runway in a handmade monochrome fit, here are some of the standout fashion events shaping the scene this summer in Chicago.
Attend a live podcast recording.
Fans of fashion history can attend a live recording of the podcast “Dressed: The History of Fashion” at the Chicago History Museum on June 10. Hosted by Cassidy Zachary with guest Jessica Pushor, the museum’s costume collection manager, the event will explore the museum’s current exhibition “Dressed in History: A Costume Collection Retrospective.” Expect thoughtful conversation and behind-the-scenes stories from one of the top costume collections in the country, according to the Fashion and Textile Museums organization. Tickets cost $80 for the general public and include access to the exhibit and the recording.
See a bold fashion showcase where Chicago design meets art and music.
We Are M-A-T-E-R-I-A-L Fashion Showcase is a gallery-style showcase that brings together Chicago designers with distinct, boundary-pushing aesthetics scheduled for June 12 from 5 to 9 p.m. at Alma Gallery. The one-night exhibition highlights the work of innovative Chicago designers including Katrin Schnabl, Gillion Carrara and Isaac Couch. With live music performances by Sam Atkins and Armand Donegan, the event combines art, music and fashion in a gallery setting. Admission is free.
Celebrate LGBTQA+ Pride Month with a DIY queer runaway.
“Rainbow Runway: A Celebration of Queer Fashion and Flair” blends fashion, activism and community. Organized by Chicago mutual aid group The Artistic Alphabet Mafia, the event takes place all afternoon on June 14 from 12 to 6 p.m. at the Chicago Athletic Association.
The event includes a monochrome-themed DIY fashion runway, textile workshops, a clothing and binder swap and a collaborative pride quilt project. Vendors and artists from Chicago’s queer community will be selling handmade textiles and wearable art. Tickets are pay-what-you-can, from $5 to $100, with proceeds benefiting Trans Chicago, a BIPOC-led nonprofit serving transgender communities.
Watch a comedy show themed fashion wearing graphic tees.
The Funny Funny Fashion Comedy Show, a monthly mash-up of stand-up and style, returns June 11, July 9 and Aug. 13 from 7 to 8:30 p.m. at the Lincoln Lodge. Each month, this comedy-meets-fashion show brings a new theme, and the comics dress accordingly. June’s show is all about graphic tees — so expect cartoons, slogans and band merch. Tickets range from $12 to $20. If you like irreverent takes on style or just want to laugh with people who understand the power of a good outfit, this one’s worth a visit.
Learn about African self-expression and culture.
Taking over the lakefront for one day only, Taste of Africa 2025: Afro-Fusion on the Beach turns Ohio Street Beach into a cross-cultural celebration of food, music and style on Aug. 16, from 12 to 8 p.m. The city’s largest African-inspired cultural event brings together modern interpretations of traditional dresses and curated market stalls showcasing designers and brands from across the African diaspora and continent. From Ankara prints and dashikis to festival-ready outfits, attendees can expect a colorful celebration of identity and expression along the lakefront. Admission is free.
Explore an outdoor market and uncover vintage gems.
Running every Sunday from May 18 through Oct. 5, Maxwell Street Market — one of the oldest cultural institutions in Chicago — blends streetwear with street food and live music with bargain hunting. Located on Maxwell Street this free-entry event features a lively mix of secondhand fashion, handmade accessories, multicultural streetwear and live blues performances. Known for its immigrant roots, the market is a destination for vintage jackets, jewelry and unexpected fashion finds. Admission is free.
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