Inside Chicago Menswear Day: the vision behind a new platform

I hadn’t thought about the need for a dedicated Chicago menswear platform in quite this way until Nikhil Kapoor reached out to share his idea for Chicago Menswear Day. He had looked at New York Men’s Day and wanted to create something with its own purpose here: less like a fashion show, not quite a trade show, and closer to a museum or art gallery, with the pieces presented on live mannequins.

The gap made sense to me. Chicago has menswear designers, retailers and people who care deeply about the clothes, but Nikhil saw an opportunity to bring them together around a dedicated platform. I wanted to support him however I could.

As he began looking at venues and sourcing what he needed, our conversations became more practical. We talked about venue deal structures, neighborhoods and event formats, and I shared advice from my experience producing events. Nikhil drove the project and brought it to life, from sourcing participants and marketing the event to finding the venue.

On October 3, 2026, Chicago Menswear Day held its first edition at One East Wacker, bringing designers, brands and guests together around the work. As an organizer and producer, I know how much goes into making a gathering happen. Good ideas are cheap; execution is everything, and I have a lot of respect for the conviction and work Nikhil put into this one.

The work and the people behind it

The invitation brought designers and brands together with tailors, boutiques, creators, media and other industry professionals. Guests could spend time with the work and meet the people behind it.

The lineup brought together custom clothing, menswear and jewelry, including Chicago custom clothing business Bespoke Below.

What stood out to me in our conversations was Nikhil’s intention to make room for menswear enthusiasts of all genders. Menswear has a history, a heritage and craftsmanship worth respecting, but the clothes aren’t only for men. Nikhil’s own style often blends masculine and feminine elements, and his vision made space for that range of expression.

I see Chicago Menswear Day as one part of a broader community that includes tailoring, vintage, footwear, watches and more. Gatherings like Sonny’s Trading Post and Stitchdown Expo bring together different parts of that world. They each have their own focus, but all create opportunities for people to discover the work and meet one another.

Chicago is a segregated city, divided in ways that include neighborhood, race, income and gender. One event cannot solve that, but conveners like Nikhil and Sonny’s creator Jabari Sandifer can help bring people into the same room who might otherwise remain apart.

Behind the scenes at Chicago Menswear Day. Photograph by Enrique Villalon.

The event’s hair and makeup team included Makeup by Meredith, Cashmere Michel’le, Krystal Mayomi, Abby Rivera and Lucia. Anino Multimedia was credited for media; Branne Newton documented the event.

A group of participating designers gathers at Chicago Menswear Day. Photograph by Enrique Villalon.

The event’s featured designers and businesses included George Patrick, Bespoke Below, Ponder by Victor Mendoza, Haochen Couture by Haochen Song, Ford General, BSBEE Designs and Takohl.

A story that continues beyond the event

The inaugural event was featured in IMBUED Fashion Magazine’s Chicago Fashion Week 2026 special issue, Beyond the Runway, Kapoor shared in a November follow-up. He also shared event photographs by Enrique Villalon and Kaliko Branne E. Newton, also identified as Branne Newton, and invited the community to revisit and share them.

The feature and photographs give the event another life beyond the room. I hope Chicago Menswear Day continues to document the work and grow into a tentpole for the community, learning and refining the format each year.

For me, the goal is awareness, access and action. People need to know about the designers and businesses here before they can find them, attend their events and shop their work. Platforms like Chicago Menswear Day and CFC’s Fashion Directory can help make those connections visible. The outcome I hope for is more people supporting Chicago’s small businesses and the fashion ecosystem around them.

Explore IMBUED Fashion Magazine in the CFC Fashion Directory. Read more: Inside Stitchdown Expo.