“Nothing against dating apps, but I think in a lot of ways digital culture is actually keeping people from connecting,” the designer Aaron Potts said on Friday. He meant in a soulful rather than a physical sense.

It was early morning on New York Men’s Day, the twice-yearly indie design event held across three floors of an industrial loft building simultaneously paces and universes away from the retail behemoth that is Hudson Yards.

Since the debut of his solo label, APOTTS, in 2019, Mr. Potts — at 50, seasoned in the fashion business — has proved himself to be nothing if not a thoughtful designer. His mostly unisex creations have drawn on references as disparate as topsy-turvy dolls, work wear, Wonder Woman, Sun Ra’s Arkestra and Giorgio Sant’Angelo, a designer New York magazine once described as a “brash, mercurial, risk-taking” supernova of the 1970s fashion world.

Mr. Sant’Angelo in particular has been on his mind lately, Mr. Potts said — specifically an image circulating on Instagram this summer of the designer on Fire Island. “There was something about the sensuality and freedom” embodied by the photo, which showed a handsome young Mr. Sant’Angelo, half-naked and festooned with bracelets and scarves, that he would like to see return. (The image was from the ’70s; Mr. Sant’Angelo died at 56 in 1989.)

A half-century ago in fashion, that brand of sensuality was anything but inclusive. Sure, Pines people connected — the term “hookup” didn’t catch on until the aughts — but the types clustered at the tea dance tended to mirror Mr. Sant’Angelo’s: muscular, pretty and white.

Mr. Potts is Black and amply proportioned. That his clothes are oversize, voluminous and floaty — think A-line dresses tiered in graduated color stripes reminiscent of Stephen Burrows; drop-crotch trousers; dress-like overshirts; covetable olive-drab overall tunics with the sides cut extra low — does not mean wearers end up looking as if they had cut armholes in a car cover. While there’s nothing remotely wrong with Lizzo — an APOTTS client — dressing in a patent-leather catsuit, Mr. Potts said, that is not to suggest that someone like her should look or feel any less sexy in a caftan.

“Whether we admit it or not, fashion makes money off the backs of our insecurities and biases,” Mr. Potts said. “I want people to feel the sensuality and lightness of whatever body you’re in. It’s taken me a long time, as a big guy in fashion, to realize that there’s no shame in a body — any body.”

Nicholas Raefksi Rocks It Old School

For the second showing of his fledgling label at New York Men’s Day, Nicholas Raefski, 25, produced a selection of graphic basics with customized circuit board prints and quirky, distinctly retro men’s wear essentials. More delightfully, he also brought along William Jonathan Drayton Jr., better known as the rapper, reality TV personality and hype man Flavor Flav. Dressed in a Raefski bomber, matching nylon trousers, a Yankees cap tipped sideways and a grille, Flavor Flav naturally accessorized it all with his signature oversize clock necklace.

“It started off as a joke,” Flavor Flav explained of the timepiece (before interrupting himself to serenade this critic with Mary Wells’s “My Guy”).

Back in the ’80s, the rapper Son of Bazerk dared Flavor Flav to replace the stopwatches he had been wearing with something the size of a hubcap. Eventually, what started out as a gag developed into a trademark and a philosophical emblem, the rapper, 63, recounted. “The reason I wear it is that time represents the most important element of our lives,” he said. Time, as he once noted on cable television, “brought us up in here, and time can also take us out.”

Terry Singh Drops Trousers

“If all the world’s a stage, then own that sucker,” Terry Singh said at a theatrical men’s wear presentation during which you would have been out of luck if you were looking for a pair of pants.

Mr. Singh, 55, a former adman of Indian ancestry, was born in Guyana and raised in Hell’s Kitchen. He wears a tidy gray beard, a topknot curled toward his forehead and — ever since returning to New York from a six-month stint among yogis in south India in 2013 — only dhotis.

“When I came back, I realized that most of our ideas of dress were still caught up in colonialism,” Mr. Singh said. “I’d always worn high-end luxury suits and suddenly I thought, Why am I constricting myself up with ties and waistcoats when I can be much more free with my body?”

Abandoning trousers, he also ditched his former profession to start the Terry Singh label. His aim? To translate the practicality and elegance of the dhoti for a Western consumer. Though initially the things he made for himself and wore on the streets of Manhattan read as “too ethnic,” Mr. Singh said, that all changed in a light bulb moment when he decided to add tailoring.

Whereas traditional dhotis are unstitched and wrapped, Mr. Singh sews in pleats, a hidden wallet pocket and buttoning waistband. The waistband detail is key, he explained, because it expands as the wearer does.

The collection Mr. Singh showed at Men’s Day featured a full line of dhoti suits with crisp Eisenhower, tuxedo or more conventional single-button jackets, cropped at the waist and reminiscent of outfits the electro-pop duo Sylvan Esso wore to the Grammys.

“I used to be inhibited about what I wore,” Mr. Singh said. “I kept my head down because I felt people were staring. Then I realized I don’t know what’s in people’s minds, and I started to dress for myself. A question I always ask people is, ‘If today were your last day on earth, what would you wear?’ Dress like that.”