How A $700 Pair Of Boots Changed The Post-eBay Clothing Resellers’ Landscape Forever

Restocking–and decluttering–your closet has never been easier thanks to online used-clothing retailers like Grailed and Twice.

How A $700 Pair Of Boots Changed The Post-eBay Clothing Resellers’ Landscape Forever
[Photo: Flickr user Marcus Ekner]

Arun Gupta just wanted some boots.


This was a few months before he began building one of the menswear world’s worst-kept shopping secrets. Specifically, Gupta found himself thinking long and hard about a pair of FBTs by Visvim, a Japanese designer brand known for its steadfast devotion to craftsmanship and all-natural materials, like black mud and indigo. It’s Americana refracted through the obsessive prism of Japanese streetwear, including the jaw-dropping price tag: A new pair of Visvim FBTs can run nearly $700.

As a fresh Yale graduate (and Yale Entrepreneurial Institute fellow) without a full-time job in 2012, such a purchase was understandably out of the question for Gupta. Irresponsible, even. And so, partly out of boredom, but mostly because he could, Gupta began coding Grailed, a secondhand online market for designer clothes where dozens of brands like APC and Our Legacy are resold by their owners. (There is also a Grailed Basic tier for lower-market brands like Topman and Uniqlo.)

Now a little more than a year old, the site attracts about 10,000 visitors a day—including the all-important eyes of fashion editors and tastemakers. Like so many startups, the site was born from the desires of the founder.

“It was mostly a fun side project,” Gupta, who recently doubled the Grailed staff to a whole two people, tells me over the phone. “I wanted people to use it, and I wanted to be able to buy stuff. I just basically wanted to get the stuff for cheaper.”

While eBay is still the ultimate spot for getting rid of pretty much anything you no longer need or want–from cars to Carhartt–Grailed is part of a new crop of online shops, along with Twice, ThredUp, and others, designed specifically to breathe new life into previously owned clothes. In many cases, these startups have wildly different business models, but they serve the same primary purposes: to cut down on waste, limit the sale of fake designer goods, and to give customers an alternative way to procure lightly used shoes, outerwear, shirts, and pants without having to sift through a sales rack.

The all-important manual that is Urban Dictionary defines a grail as “the shoe shoeheads and sneakerheads want the most for their collection,” which is mostly correct, only the term has since evolved to apply to any coveted piece of clothing. It’s a term that is thrown around regularly in menswear forums like StyleForum, SuperFuture, and Reddit’s r/MaleFashionAdvice. A grail is uniquely personal; my grail isn’t necessarily yours.

advertisement’s architecture is designed to provide people who traditionally would have had to sell and trade their clothes on forums an intuitive way to browse, as if they were shopping on Before Grailed, if someone wanted to sell, say, this $4,500 goat-fur parka by Helmut Lang, they had to create a new post with their asking price, embed an image hosted on another site like Flickr or Imgur, and monitor their replies. If another user made an offer, they would have to coordinate the exchange over email, and conduct the transaction via PayPal.

Grailed takes out a lot of the intermediate steps by arranging everything into a browsable grid that users can arrange by designer, type, and size. Once a purchase is made, the transaction—and any relevant disputes should the item never reach its destination, or maybe if it’s a fake—are handled by PayPal. “I know a lot of people have issues with PayPal from a consumer standpoint, but from a business standpoint, PayPal has been fantastic,” says Gupta, who says that lists as many as 10,000 products a day. “They have really good buyer and seller protections.”

Gupta declined to discuss his plans for monetizing Grailed just yet, and insisted—as the startup-guy refrain tends to go—that he’s focused on trying to scale. “The sell-through rate is so quick,” he adds. “Seventy percent of stuff sells in the first two weeks.”

While Grailed caters exclusively to the menswear market, a handful of other sites in San Francisco are aping the consignment store model for online. One of the more notable (and, at least in my opinion) useful models is Twice, a three-year-old company based in San Francisco that has raised $23 million from Andreessen Horowitz, among other VC firms, that makes it easy for both men and women to buy and sell used clothing.

The service works like this: First, it sends you a huge plastic bag to fill up with your lightly used resellable clothes. After loading it up with the stuff you don’t want, and double checking that it’s an accepted brand on the website (Banana Republic, J. Crew, and Ann Taylor, for example), you mail the bag back to Twice. Shipping is covered by the company.

If your gear is in good condition and Twice accepts your clothes, you get either cash or an extra 25% bonus credit to use in the store. It’s consignment gone digital. No need to throw your rags in a big blue Ikea bag to schlep 10 pounds of stuff downtown. “[Twice] was born out of a frustration with eBay,” says cofounder Noah Ready-Campbell, a former product manager at Google. “We knew it was fun to shop on eBay, and merchandising is fun and awesome. But selling on eBay was such a pain in the butt.”


Twice essentially does all of the work for you. If they don’t accept your clothes for whatever reason, you can pay a fee to have it shipped back to your home, or the clothes get donated. It also handles all the inventory, too: Everything Twice sells is stored in a 25,000-square-foot warehouse in San Francisco. It’s a full-scale operation.

“We buy from our sellers,” says Ready-Campbell, who notes that the company has about a million users overall and has processed 150 tons of apparel and accessories, which it kept out of landfills. “We photograph it, merchandise it, and sell it.”

Some analysts speculate that fast fashion—or the kind of cheap-to-produce, trend-driven commerce churned out by Forever 21 and H&M—is on the decline, and a new wave of young consumers are instead focusing on buying fewer, high-quality pieces. In other words: buy less, but buy better. Only that argument doesn’t quite hold up to scrutiny: Last year, for example, Zara earned $19.7 billion in sales, while H&M notched $20.2 billion in sales, both up from previous years. An analysis by Euromonitor concludes that fast-fashion retailers have an “unbeatable competitive edge” and are, therefore, “here to stay.”

But the rise of online re-retailers post-eBay–and look no further than Nasty Gal for a crash course in this–indicates pretty clearly that there is a market segment of consumers who might want to declutter their lives, especially if they wear the same four or five things every day. They can’t be ignored. Om Malik, the investor and technology writer, for example, is selling the unused portion of his designer-rich closet on Twice, and donating the proceeds to charity. It’s a fascinating promotional model that Twice cofounder Ready-Campbell is excited about. (Twice is also working on a similar closet-emptying spree with Golden State Warrior star Andre Iguodala.) As Malik wrote in a beautiful meditation on his blog:

Deep down, for [the] past few years I have known that I had accumulated too many things. I was holding on to things–both physical and metaphorical that provided the comfort of past, leaving room for nothing new. I was holding on to things that didn’t make any sense. I didn’t know why I had a living room full of furniture that had started to feel so alien.

Today, I much prefer few things–well fitting, mostly bespoke, and built to last into the future when I might be long gone. The mainstream brands have little room in my life, instead I prefer to find craftsmanship. I like makers who make, because they don’t know what else to do. These choices are hard, sometimes cost more and take a lot of patience. I have learned to buy things I love. There isn’t any more room for mere “likes” in my life.

Finally, one of the other advantages is that reselling makes big purchases less of a financial gamble for customers. “One of the reasons I was so excited about Grailed is because it makes it so much less of a risk if you buy something expensive,” says Gupta. In a way, the secondhand economy strips retail of its latent consumerism and bends that appreciation toward the clothes themselves. It’s less about patronizing brands and more about liking well-made things for what they are.

While Gupta says he still personally peruses Grailed every day, he admits that he never did find that pair of boots. Which is fine. Because now his grail is a new jacket.


About the author

Chris is a staff writer at Fast Company, where he covers business and tech. He has also written for The Week, TIME, Men's Journal, The Atlantic, and more