The Tim Gunn of “Project Runway” seems perpetually dapper. As he advises competitors to “Make it work,” he barely appears to have to work to seem put-together.

It was not always so.

Born in 1953, he began dressing himself in the swingin’ ’60s. “The bell bottoms and the crazy prints and the floral shirts, it was awful,” he admits. He didn’t fully begin to embrace a personal style until he was chairman of the Fashion Dept. at Parsons School of Design in New York, where he got a scolding from designer Diane von Furstenberg.

“She said, ‘You can’t be in this industry and look like this.’ And I said, ‘Well, what should I do?’ She said, ‘I’m not going to tell you that. I’m just going to tell you this won’t work.'” A period of all-black outfits followed, but eventually he moved on to the look we see today. “So we can keep evolving, I have to say.”

Gunn’s “Make it Work” Shortlist features three fashion-centric films that can provoke self-examination and evolution: “Darling,” a less-than-flattering portrait of a model in 1960s London, and two documentaries centered on Vogue Magazine: “The September Issue,” focusing on Vogue at its peak under Anna Wintour, and “The Eye Has to Travel,” about one of Wintour’s famed predecessors, Diana Vreeland.

Watching “The September Issue,” says Gunn, left him impressed with Vogue’s creative director. “Grace Coddington is filled with integrity and purpose and she has a vision of what’s best for the magazine, and she’s the person you’re rooting for.”

Gunn is a longtime fan of Vreeland, subject of “The Eye Has to Travel.” Vreeland, he says, loved problems that needed to be solved. “She saw them as personal challenges. She was going to rise, not fall, so for me, she’s the make-it-work icon.”

At Parsons, Gunn had movie nights for the students. He often showed “The September Issue.” To represent the 1960s, he would show “Blow-Up.” Now he wishes he’d shown “Darling.” “It is so much more profound,” he says. “[‘Darling’] is a film that causes you to search your own values.”

“I found that these movie nights were just a tremendously important enhancement to the education that the students were receiving. And for me, while technique is certainly important, the conceptual process is always the more important aspect. What do you want to say? Who are you as a designer? You can’t just make clothes. It’s about having a vision.”

To watch Gunn’s “Make it Work” films, “The September Issue,” “The Eye Has to Travel,” and “Darling”* and other movies like these, start your Tribeca Shortlist free, seven-day trial here.

*Titles subject to availability