In the window of the New Museum this month, the performance artist Justin Vivian Bond plans to periodically strike a pose in a pink gown with rhinestone teardrop, framed by hand-drawn wallpaper twinning the artist’s face with that of the former Estée Lauder model Karen Graham. As a closeted transgender teenager in the 1970s, Bond obsessively drew Ms. Graham, until “I made myself my canvas.” The artist is wearing a vintage dress by Frank Masandrea, one of several little-known couturiers who outfitted Ms. Graham before AIDS cut them down in their creative prime.

The project, “My Model | MySelf: I’ll Stand by You,” proudly puts what Bond calls a “queer face” on the glamour created by gay people that has long been appropriated by mainstream culture. The designers “served the aspirational whim of wealthy upper-class white women and then were completely dismissed by history,” the artist said.

Bond is one of more than 40 intergenerational artists in “Trigger: Gender as a Tool and a Weapon,” opening on Sept. 27 with work that explores gender beyond the binary of “male” and “female.”

It is the largest show to date at a major museum to tackle gender fluidity, which has become native to young people who are used to constructing their own identities on social media and declaring their preferred personal pronouns on college campuses and at workplaces. And as the highly charged debates over transgender rights swirl in the news — from President Trump’s call for a ban on transgender service members in the United States military to the laws governing access to public bathrooms and locker rooms to harassment in prisons — “Trigger” brings a new level of visibility to gender-fluid artists who have only been acknowledged before in a trickle of mainstream shows.