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Photo: Anastasia Garcia

After Hey Gorgeous Shutters, Its Founder Says Plus-Size Has a Long Way to Go

The beloved plus-size startup went under after failing to nab investors.

Racked is no longer publishing. Thank you to everyone who read our work over the years. The archives will remain available here; for new stories, head over to, where our staff is covering consumer culture for The Goods by Vox. You can also see what we’re up to by signing up here.

In 2013, Aimee Cheshire, a former model and blogger, decided to launch a digital plus-size fashion boutique.

The plus-size industry seemed ripe for opportunity, bringing in $17.5 billion in sales between May 2013 and April 2014. And with good reason, considering 65 percent of American women fall into the plus-size category (size 14 and up). The market somehow is still considered niche, though, and aside from a select few brands, there weren’t many places shoppers could proudly turn to for fashionable, plus-size choices.

Cheshire envisioned her company, which was first called Madison Plus Select but was then rebranded as Hey Gorgeous, would be one that challenged stereotypes and supported the slew of independent designers and bloggers who were diving into making plus-size clothing themselves, rather than waiting around for retailers to wake up. Hey Gorgeous lived as an e-commerce site, and one that was daringly inclusive: It carried sizes 8 through 24 and sold mainstream fashion brands as well as plus-size ones.

Perhaps more importantly, Cheshire also set up Hey Gorgeous’s New York office to live as a distribution center and showroom. Shoppers who were used to ordering clothing online or requesting a larger size be sent to their homes because plus-size wasn’t kept in stores could finally try on clothing (“I just spent 2 hours in the Hey Gorgeous showroom for a private shopping session and it was such a wonderful experience!” read one Yelp review. “I don't shop, I hate to shop because nothing fits me, and I am now going to tell you how much I loved shopping today!”) Cheshire had dreams of offering this experience elsewhere, telling Fashionista that she hoped to eventually open showrooms in Los Angeles and Chicago.

The Hey Gorgeous New York showroom.
Photo: Aimee Cheshire

Two years in, though, and Cheshire found herself in a financial debacle, where, as she told Racked, she could “barely keep the lights on.” Hey Gorgeous quietly shuttered in October 2016. With its failing, Cheshire now reflects on the plus-size market and believes that while progress has been made, Hey Gorgeous going under “shows me that there still is a long way to go.”

The trouble started for Cheshire last May, when an investor Cheshire is choosing not to name pledged a whopping $100,000 investment. Hey Gorgeous had previously raised $1.5 million in three rounds of seed funding, which helped Cheshire get the company off the ground and operate smoothly for a little while. But Hey Gorgeous needed more to continue to operate while it expanded (a general consensus is that it takes an average of three years to properly build a business). The brand’s operating costs were about $30,000 a month, Cheshire says, between running the e-commerce site, renting an office space, buying inventory, and paying four employees. (Cheshire says she was not getting a salary.)

Cheshire says the $100,000 pledge ignited the interest of three other investors, who told her they too would fund Hey Gorgeous once the $100,000 came through. It never did. After following up with the first investor month after month, it became clear to Cheshire that the money was never going to come in.

“We pressed forward and did a lot with very little, but the goals were impossible to meet without any funding and it put us in a continuous downcycle,” she says. “We started to be in debt to vendors we owed money to. We were locked into huge buys of inventory and we had to pay up front because we were buying from smaller, independent brands who used our money to manufacture.”

Aimee Cheshire of the new-defunct Hey Gorgeous.
Photo: Lily Cummings

Cheshire says her brand eventually entered deep water at the beginning of the summer: “Eventually, we had to back out of orders we placed, which was sad because we were one of the few places where talented designers could sell to.” She tried to find other investors, but summer is a particularly difficult time to raise money (since investors are traveling and on vacation, because money).

In August, Cheshire and her business partner David Wechsler decided to pull the plug. Hey Gorgeous began cleaning out inventory, pinging loyal customers to get first dibs before closing the company completely in October. The saga was a low blow for a venture that was praised by Racked and plenty of other publications as one of the most influential plus-size businesses out there. Brands Hey Gorgeous carried, like New York-based luxury brand Shegul, took the news particularly hard.

“It was quite emotional, as Hey Gorgeous was the pioneer in terms of supporting indie designers where big players shy away,” says Aysegul Ilter, the CEO of Shegul. “It gave voice to new brands entering to the market, providing a much-needed platform, supporting [us] both financially and emotionally. They took risks and nurtured brands such as Shegul. Being a pioneer and setting the stepping stones for other brands also cost them.”

The news also devastated shoppers who didn’t just turn to the brand for clothing, but also saw it as a supportive gesture.

“When Aimee started [her blog] Madison Plus Select, and then Hey Gorgeous, she was filling a very real gap in the industry,” says Amber McCulloch, a Chicago-based blogger and Hey Gorgeous customer. “At the vast majority of stores, the plus-size sections are hidden away in the back corner of the store, or relegated to online-only offerings. Her site and her showroom brought together the best plus-size designers in the business with their ideal customers.”

Back in 2014, Cheshire told Racked that some of the brand’s biggest hurdles included convincing plus-size shoppers to invest in good, quality clothing: “Our customer hasn't been conditioned to enjoy fashion in the same way as her straight-size sisters,” she said at the time. “It's always been, ‘I'm gonna lose 20 pounds,’ so they'll hold off on shopping. One of the most unexpected challenges is getting women to change their attitudes towards themselves.” Hey Gorgeous struggled with some of its customers, witnessing loyal shoppers alongside those who would drop off the map after one purchase, especially those who wore smaller sizes (presumably because they went to shop at non-plus brands).

The company also saw an extremely high return rate, with vanity sizing to blame; customers often ordered dresses in several sizes to feel the styles out and it was often at Hey Gorgeous’s expense, as the brand was covering shipping both ways. Hey Gorgeous also struggled to build brand awareness; it didn’t exactly have the budget to advertise boldly and noisily the way other plus-size brands do (remember those subway ads from Lane Bryant?), and so even though Cheshire was essentially a poster child for Hey Gorgeous, since she was well-known in the space for her blog, the company failed to reach big-league exposure. The business model didn’t help this glitch, either; customers who took to Hey Gorgeous’s clothing became loyal to the brands it sold, but not necessarily the company as a retailer. Last June, Hey Gorgeous debuted its own T-shirt line, but the move proved to be too little too late, given the startup’s finance troubles.

Photo: Lily Cummings

But even while admitting that there were many errors that fell on her and her team, Cheshire now concedes that hacking Silicon Valley was her biggest challenge.

“You are dealing with people who don’t understand the space,” she says. “I actually had someone ask me, ‘Are you different than Saks or Bloomingdale’s?’ Because they don’t even know that Bloomingdale’s hardly sells any plus-size!”

McCulloch agrees the business world has different standards for the plus-size industry. While there’s been some momentum — like Gabi Gregg, the blogger behind Gabi Fresh who was able to launch her own swimsuit line — McCulloch says investors still don’t see the plus-size space the same way they do mainstream, and that’s clear based on the way the actual clothing is treated.

“It's extraordinary to see how much the industry has changed just in the past two years. What's more extraordinary, though, is that the majority of mainstream retailers and high-end fashion designers and investors are still ignoring the power of this consumer, or worse, treating us like a dirty little secret,” says McCulloch. “If they do offer plus-size collections, many of them spend absolutely no money on marketing — their plus-size offerings are left out of their fashion shows, their catalogs, their social media images, and even the in-store events that large department stores host for their patrons. Website images of the plus-size collections are often modeled by size 8 or 10 women who do not do justice to the clothes.”

The same can be said of the fashion press. Hey Gorgeous has been gone for over four months, and yet no one reported on the brand shuttering. Cheshire admits she closed the brand quietly, but as Sarah Conley, a blogger and Hey Gorgeous fan puts it, when it comes to plus-size coverage, “the focus is still heavily on the latest celebrity line or when a celebrity claps back to a ‘hater’ instead of looking critically at whether or not the actual plus-size customer is being served.”

Conley sees how it could be “difficult for investors (on the surface, of course) to understand the value in playing in the market at different levels because the only press coverage they typically see is the community demanding more, or businesses not doing well.”

Hey Gorgeous seemed to have it all in the cards — at least in the beginning, anyways. Customer response was immensely positive. The business was off to a good start, too; Hey Gorgeous had a database of almost 4,500 in 32 countries (the brand declined to share sales figures, but says there was 100 percent annual growth year-over-year).

So why weren’t investors keen on opening their wallets to Cheshire? She believes plus-size shoppers just can’t escape prejudices. As Dallas Thompson wrote for Racked earlier this month, “The worst part of being fat, in my absolutely-not-humble opinion, is that retailers like you, J.Crew, look at my money differently than they look at skinny-people money. You seem to think that my money is worth less because my ass takes up more space.”

Photo: Hey Gorgeous

“A lot of people have a natural bias toward plus-size shoppers, whether or not they like to admit it; they think less of the person who is overweight,” Chesire adds. “The tech world is male-dominant, and it’s not where these men are putting their money.”

Post-Hey Gorgeous, Cheshire admits direct-to-consumer seems to be the only way to approach fashion; it’s how essentially every market, from accessories to shoes to bras, is seeing growth, and so plus-size needs to follow suit. And Cheshire isn’t giving up on the space just yet. After all, the potential for opportunity is basically low-hanging fruit at this point. NPD found that the annual sales of women’s plus-size apparel rose 17 percent over the past three years, from $17.4 billion in 2013 to $20.4 billion in 2016. Cheshire says flatly that “anyone who is only interested in getting involved in retail companies that sell size 12 and under just isn’t forward-looking. Because plus-size is the only space in retail that hasn’t yet been developed.”

Case in point? The plus-size fashion brand Eloquii. It started out as a quiet, niche line launched by The Limited in 2011 — one that the brand didn’t make very visible to begin with. In 2013, The Limited quietly discontinued Eloquii. But the brand bounced back on its own, resurrecting as an e-commerce venture after members of its original staff obtained private investment from Gilt founding member John Auerbach.

Back in 2015, Eloquii CEO Mariah Chase reflected on the struggles of the space, telling Racked, “between finding space and finding investors, it’s hard.” Today, though, Eloquii is hailed as the most successful brand in the space; one that saw an annual growth of 165 percent during 2015, according to reports. Last year, it nabbed a $15 million investment in a Series B round of funding. That’s worlds away from its former parent company that tried to kill it: The Limited filed for bankruptcy last month, news that came only days after Racked reported it was rushing to close all 250 of its stores.

As McCulloch puts it, “Eloquii proves that if plus-size women are offered trendy designs, careful fit, quality fabrics, great price points, and inclusive, upbeat and visibly plus-size advertising, they will buy — and they will keep buying.”

Cheshire has since moved on to a different up-and-coming plus-size brand and will continue to press on in the space, not just because she believes plus-size shoppers deserve a fair choice at fashion, but because “the profits that could come from this market could be tenfold.”

Those that fail to see the potential? “Too bad on them.”

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