Some guys can rattle off every relevant stat about their favourite team or player. Other guys, like Chad Kramer, who recently took the reins as CEO of Del Toro, the footwear brand known for Italian-made velvet slippers and suede and leather loafers? Well, not exactly.

“I’ve always been a huge menswear and fashion nerd. Like, obsessed with this industry,” he tells me over Zoom. He’s in Chicago, I’m in Brooklyn, and we’re chatting about his affinity for menswear’s digital heavy hitters. “They’re like athletes to me,” he continues. “Even my friends back in Chicago are like, ‘You know more about menswear designers or influencers than you do about the current Chicago Bulls team.’ That’s how big of a dork I am.”

Kramer joined Del Toro in November of 2022, but his move into the fashion industry has been a long time coming. He started out working in finance at J.P. Morgan, first in Chicago and then in New York. “I loved it for the first few years,” he says, “but then I realised that I still do have this fashion itch.” To scratch it, He enrolled in Parsons School of Design's one-year fashion entrepreneurship program to relieve that itch.

“I lied to my coworkers and told them that I was going to business school at night,” he laughs. “I’d wait for them to leave, go into the bathroom and put on what I thought was cool, lower-Manhattan gear, then look out of the bathroom like, ‘All right, is the coast clear?’ and run out of 270 Park Avenue, get on the subway, and go down to Parsons.”

Just after he finished up the program, life brought him back to Chicago, and eventually out of the finance and into tech. He took a job at Meta, working mostly with McDonald’s, but kept the fashion flame burning by connecting with some of his menswear “athletes” and helping them out with stuff like Instagram verification. Then, everything came together because of a jumper and a fateful dinner party—not to mention the increasingly permeable wall between the worlds of fashion and technology.

“I went to dinner with a bunch of other parents of young kids wearing an Aimé Leon Dore crocheted vest,” Kramer says. “It was pretty bold, but I was like, ‘I can pull this off in the suburbs of Chicago!’ One of the guys there, a friend of mine, said, ‘I don’t what the hell you’re wearing, but a buddy of mine just bought this shoe company called Del Toro. Have you heard of them?’”

Kramer was incredulous. Del Toro was founded in 2005 by Matthew Chevallard and built up something of a cult following during the #menswear era, when items like the brand’s signature velvet loafers were littering Tumblr feeds alongside super-slim Italian tailoring and extremely high-and-tight haircuts. That era passed, and Del Toro was sold in 2018 to a group of investors (Carmelo Anthony among them). Those investors’ plans fizzled and it was sold again in 2020. By the spring of 2022, Kramer was convinced the company was kaput.

After being disabused of that notion, he asked if he could meet the new owner, just to hear his story. “Forty-eight hours later, my buddy sends me a text that says, ‘Don’t kill me, but they need a new CEO, and I sold them on your background,’” Kramer explains. “I was like, ‘What?!’”

Cue the whirlwind of interviews and presentations. Then the hire. Kramer started as CEO in the midst of the holiday season—“the most fun and chaotic thing I’ve ever done”—and after weathering the storm, started the project of “bringing people back to Del Toro” in earnest.

That necessitates a three-pronged strategy for Kramer. On the one hand, there are those velvet slippers, which continue to be a brand favourite. “There’s no denying it: the black velvet slipper is our hero item,” Kramer says. “When I’m in Chicago or visiting friends in New York or in the suburbs up here, there are people coming up to me saying, ‘I wore Del Toro tuxedo slippers to my wedding.’ That’s so cool.”

“Nobody owns the men’s wedding shoe space,” he continues. “No one really says, ‘Those are the go-to wedding shoes.’ That’s who we want to become.”

Del Toro is also targeting the sports industry when it comes to occasion-specific attire. or at least the world of "country-club sports. “What is the shoe that you wear to the golf course, and the shoe that you slip on as soon as you get off the course?” Kramer asks. He’s hoping it’ll be something like the Centesimo, made of unlined goat suede, or the flagship Milano loafer in calf leather.

Making things official, Del Toro is the footwear supplier for the U.S. Team at this year’s Ryder Cup in Rome. “That is us breaking through to golf,” Kramer says. “We are putting our foot forward and waving our hands and saying, ‘We are here. Hey, golf guys, pay attention.’”

The last piece of the jigsaw is persuading males who prefer Vans Slip-Ons and Birkenstock Bostons that there is another way to go about things. Loafers are "knockaround shoes," according to Kramer, so men shouldn't worry too much about them. Just shuffle them on with whatever and walk out the door.

“That’s how people are getting dressed today,” he says. “They’re staying comfortable, but they’re also leaving the house again, so they want to get dressed. And it’s such a layup to put on a pair of loafers. We’re not just a shoe to wear with your business casual when you go to the office. We’re also a shoe to wear hungover when you go to the bodega on a Saturday morning.”

“We could really encompass every aspect of daily life,” Kramers says. “It’s a huge challenge, but it’s one that gets me really excited.”

Originally published on Esquire US