The Founder of Plus-Size Shopping's Most Popular Boutique on Fashion and Inclusivity

This is why Aimee Cheshire, a former plus-size model and fashion blogger, started Hey Gorgeous. The site, which launched last year, is a curated plus-size fashion boutique stocked with a variety of designers—contemporary as well as indie.

Racked caught up with Cheshire to discuss the start of Hey Gorgeous, the difficulties plus-size shoppers face, and her recent foray into fitness apparel.

Model Dianna D’Amore in a Hey Gorgeous look.

How did you get your start in fashion?

I started out studying psychology but soon realized I wanted to get into fashion. Creating fashion was something I wanted to do but I always felt like an outsider. Growing up, I was the big kid. I was always in jogging suits, and my first pair of jeans that actually fit were men’s jeans. I got a fashion merchandising degree in New York from LIM and worked as a plus-size model but quickly realized that that wasn’t really what I wanted to do. I got a job at One Stop Plus, which was the only plus company in New York at the time. I did product development there and left in 2009 to start my blog, Madison Plus.

And that led to the launch of your clothing company?

Through my blog, I developed great relationships with models and designers in the plus-size space. They really had nowhere to go. They were too small to get into places like Nordstrom and Macy’s, which weren’t really focusing on plus at the time anyway. I wanted to create a site that supported these indie designers and also more mainstream brands. I wanted to cater to women who wanted to shop at a site that was dedicated to them, not a side project that a company was doing to sort of address the market.

What was plus-size shopping like at the time?

Lane Bryant was the only option, or Avenue. When I used to go shopping, I would be creative, which is what a lot of plus girls do. Anthropologie occasionally makes plus size XL, and Gap and Old Navy made larger sizes. But it was really hard to find anything that fit that was fashion forward.

The problem was there were contemporary designers whose clothing I wanted to spend money on but they didn’t make my size. How many times did I go into Intermix and try on an item that was stretchy or trapezy!

Why do you think there’s such a void in the plus-size space?

It’s kind of crazy. When I was a kid, I thought that by the time I was in my thirties, there would be plenty of options for me, but the market’s really underserved. The majority of people in the fashion world assume that anyone who is plus wants to lose weight and be one of them. It’s changing now, though: the power of the internet has a lot of girls knowing that they’re not alone in being plus, that there are other people out there like them.

Aimee Cheshire. Photo by Lily Cummings

How is Hey Gorgeous different from other plus-size retailers?

We curate. We work with many designers and major brands to curate their collections. People assume that everyone in the plus market wants the same thing. So they think, “just give them some T-shirts, some pants, and they’ll be happy.” But when 50 percent of the US population is plus, there are a lot of personality types and a lot of different styles and women who want different options. It’s taken longer for people to realize there’s not just one type of plus-size woman.

How do you decide what to carry?

I try to have a good mix and get creative to find pieces that no one else would have. Usually, there are two blanket style options for plus women. It’s either a bodycon dress, like cheap spandex, hugging all the curves and showing chest and legs, or baggy clothing, like trapeze-style shapes with three-quarter length sleeves. We want different fashion choices. I try to find the piece that makes you want to say, “Oh, I’ve been looking for that forever, finally someone has it!”

“One of the most unexpected challenges is getting women to change their attitudes towards themselves.”

How did you get the business of the ground?

I met my business partner, Dave [Wechsler], at the Facebook offices at a Women in Tech meet up. He started grilling me on the plus industry—he had no idea that it existed and was impressed by the opportunity. We started to work together and then it really just took off. Dave has been able to raise over $22 million for his past companies and with my knowledge of the plus-size industry and idea of what I wanted to bring, we started Hey Gorgeous.

Was it hard to get investors?

It was. It’s a world people aren’t used to investing in. It took some digging to find someone who really believed in this woman and believed in changing the attitude towards plus size.

What will it take for plus-size fashion to become mainstream?

It’s not helpful for us to take time complaining that Victoria’s Secret doesn’t offer our sizes. Let’s not focus our energy on who’s not giving you what you want and focus our energy on supporting the brands who are. We need to create our Victoria’s Secret. Let’s create our own brands that want our business. That’s an important mind shift that people have to make in order to help the plus industry grow.

An Adrianna Papell dress.

Who do you like working with right now?

I love our BB Dakota collection; they’re a great name brand to address the straight-size women as well and they don’t compromise their fashion for the plus girls that they service. I love Ply, our new indie designer, as well as Line & Label. Adrianna Papell does fabulous-fitting dresses for all sorts of occasions. ABS is great, and so is Tiberia, a small designer who has really fun, quirky prints and dresses. We’re also now working with Stephanie B, a designer out of Toronto who does some exclusives for us; her Elle Dress is one of our best sellers.

What are your biggest hurdles?

Our customer hasn’t been conditioned to enjoy fashion in the same way as her straight-size sisters. It’s always been, “I’m gonna lose 20 pounds,” so they’ll hold off on shopping. But we want women to know that they can look great now. Don’t punish yourself. One of the most unexpected challenges is getting women to change their attitudes towards themselves.

How do you feel about the athleisure wear trend?

We actually just starting selling activewear. I know there are strong stereotypes that plus women don’t work out and don’t want to be in that situation, but that’s incredibly incorrect. Just because you’re plus doesn’t mean you’re a couch potato. And that’s why we want to sell activewear.

What are your hopes for Hey Gorgeous?

I would love to launch collections with more mainstream designers like the DVFs of the world. I also want to create an authentic and welcoming place for women to shop so they can play in the world of fashion. The possibilities are endless.

Read more of Racked’s Ladies Who Launch!

The Founder of Plus-Size Shopping"s Most Popular Boutique on Fashion and Inclusivity