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Grailed CEO Credits Success to the Metrosexual Movement

Grailed wants to help you look like the best version of the “urban ninja” or “lumberjack” or “1950s farmer in England” that you want to be.

At the Luxury Interactive conference in New York City on Oct. 16, co-founder and CEO Arun Gupta credited the metrosexual movement of the mid-2000s with allowing men to openly care about grooming and spending money on expensive fashion. Gupta admitted Grailed capitalized on the online communities and forums already fanatical about men’s fashion back around 2012 and activated that passion by adding in the commerce element because, he pointed out, “forums are not a good place to transact.”

Now Grailed is a top online destination, a peer-to-peer marketplace for hypebeasts in search of the latest must-have product or hard-to-find Public School, Raf Simons, Rick Owens and “weird esoteric brands from Japan.”

Grailed, Gupta said, stands for men’s fashion, but even more so, it sees itself as democratizing access to fashion. Maybe you live in Middle America or don’t have the income typical of a luxury shopper; maybe you wouldn’t feel comfortable setting foot in a tony Yves Saint Laurent boutique. But log onto, and not only can you find what you’re looking for, but you know it’s a sound investment. Because, Gupta noted, if a user can sell you jeans for $300, then you can turn around and recoup your purchase price, too.

Though the site’s community members were important from the start, in a sense they’ve shaped the platform’s direction. Grailed is the place where someone can show off his unique style, which often attracts others with similar interests furthering the community in a deeply authentic way.

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Organized as a running feed of products on its main page, Grailed helps users discover brands previously unknown to them. Prospective users that convert to Grailed power users are the ones who start off searching for one thing but are intrigued by fashion in general, so they’re completely captivated when they encounter the site’s expansive world of goods they didn’t know existed, Gupta said. There’s a “powerful, emotional resonance” to that moment, he added.

Grailed’s “coming out” moment came three years ago with the launch of the now-annual Grailed 100, a curated list of 100 memorable pieces from the past two decades of men’s fashion, all pulled together on a beautiful, shoppable page. It was Grailed’s first marquee brand activation, Gupta explained, and a shameless ploy to garner earned media—a way to “get our name out there and plant our flag in the ground.” Shoppers browsed a veritable who’s who, including Undercover Leather jackets, Number (N)ine—the Japanese brand with a cult following—and a pair of Rick Owens dunks, the high top sneakers bedecked with a ripped-off Nike swoosh and in production for just two years before the athletic giant forced the designer to cease and desist. (Never-worn deadstock sells for $5,000, Gupta noted.) Sought-after L.A. photographer Nicholas Maggio, who has shot for Adidas, Cadillac and Puma, was brought on to capture the 100 in a way befitting such rarefied stannable finds.

Grupta likened the very first Grailed 100 to a “beacon for the community” that the men’s style has a new voice and it’s “propelling men’s fashion like no one else.” That moment also turned Grailed onto the important of content in commerce, prompting the launch of an editorial section of the site entitled “Dry Clean Only.” Because the brand is not “beholden to advertisers,” Grailed, which takes a 6 percent commission fee, has “infinite creative license” to pursue its point of view—what’s cool and interesting and relevant to the community. Dry Clean Only is where users will find “master classes” on specific designers and teachable moments, such as a reflection of tie-dye through the ages or SoHo street style, Gupta said. Though one day editorial might evolve into a customer acquisition vehicle, for now it’s an indispensable means of reinforcing the Grailed brand, he added.

Grailed might be a marketplace, but it very much does not want to be an Ebay. Because it carries product across the high-low spectrum, it serves a broad range of consumers. The challenge, according to Gupta, is to strike the right brand tone so no one feels excluded. The fashion insider might be able to rattle off a dozen luxury brands, while on the other hand, “there are people who don’t know who Gucci is but they care about style and what they wear,” Gupta explained.

As the market for men’s fashion shifted, Grailed evolved accordingly. Red-hot product drops, Gupta said, have hugely affected how people shop. “It wasn’t about reselling luxury but about buying the coolest, trendiest-hype stuff,” he said. Grailed got its first “inkling of the drop hype movement” with the H&M collaboration with Balmain, which “flooded” the site, but then came the Yeezys, which were an even bigger sensation. Because those drops inundated so much of the same product onto the site so quickly, Grailed ended up dividing it into four market sections: Grails, for high-end designer goods; Hype, where users find sneaker drops and streetwear; Sartorial, for a man’s suiting fix; and Core, which carries, thrift and vintage finds, and the mass-market likes of Gap and J. Crew.

Some drops might add too much sameness to the homepage product feed, but others, like Supreme’s collab with The North Face, generated $1 million in sales in a single day, Gupta said, adding, “It was hard for anyone to foresee the rise of Supreme.”

As a community, Grailed is in a constant state of flux and will continue to be as trends wax and wane. “Men’s fashion has changed a lot in past three to four years,” Gupta noted. “At our core we’re a function of what’s popular in the marketplace.”