A Plus Size Fashion Exec Talks Body Image, Modeling and High Style

Photo: Lily Cummings Photography

There may be a sea change afoot in the world of plus size fashion, but try to actually shop one of Manhattan’s tonier boutiques as a size 16 woman, and you’re likely to feel like nothing’s new. Aimee Cheshire, a 35-year-old Brooklyn-based fashion executive and former plus-size model and blogger, knows the feeling well.

“I’d be at investor meetings and I’d get pushback. They’d say, ‘How do you know this woman really wants to spend money on clothes?’ says Cheshire. “I’d turn around and say ‘There is not one store in this neighborhood where I can walk in right now and spend my money.’” 

In 2014, Cheshire, along with her business partner David Wechsler, founded Hey Gorgeous, now one of the fastest growing online resources for affordable, luxurious clothes in sizes 8 to 28. The site, which has earned high profile fans like models Emme, Leila King, and Danielle von Grondelle, sources on-trend pieces from lines like BB Dakota and Jessica Simpson as well as boutique brands like Brooklyn’s Line & Label or the Danish collection Carmakoma. 

Related: Candice Huffine: The Plus-Size Model Who Is the Ultimate Muse Among Fashion’s Skinny Set

Today, the plus-size market accounts for some $16.2 billion in sales annually, but Cheshire says she’d like to see that grow (and she’s happily picking up the slack from department stores who choose not to offer plus size clothing on their sales floors.) 

“It’s about time the industry got beyond the model of making $12.99 shirts for the masses, who they assume have no sense of style. These shoppers have been pushed out to the fringes, and they’re sick of it.” 

Yahoo Style: When you arrived in New York in 2003, you were a plus size model for a while. What insights did that give you into how the plus size industry works? 
Aimee Cheshire:
I studied psychology as an undergraduate and then came to New York to do fashion merchandising. I put two and two together. I thought, I’m tall, I’m pretty, what are my options to make money while I’m in school? I find in the plus community there’s lots of women who want to be models. Getting that outside validation from people, that acknowledgment that “You’re pretty as well, even though you’re not the standard,” I think I was experiencing that craving for approval. I did more mainstream things, like fashion shows at Macy’s, but I found myself walking a little taller. 

Courtesy of Hey Gorgeous

YS: Were you under pressure to conform to certain standards? 
AC: When I started, I wasn’t used to being looked at. I was more used to hiding or just sort of blending it. It was a big challenge for me to get over. I did notice the fact that I had to lock into the weight and size my contract said I needed to be and that was a little nervewracking to me. As a plus size model, you still have to be fit, you have to find that ideal hourglass shape, and I carried my weight differently, so my figure wasn’t that ideal plus size figure. There’s no winning, really. 

Related: The Body Image Book Is Changing the Plus Size Conversation

YS: After that you delved into the business of creating and selling plus-size fashion. 
AC: 
I was in school for fashion merchandising and I knew after dipping my toe in the modeling world that it wasn’t a long term thing. At the time, there was only one company based in New York that did plus size fashion: One Stop Plus. So I started an internship and was hired straight out of college and started creating garments with a big mass retailer. My average price point for a top was $12.99. It was my training ground, where I learned what the customer wants, why there were hurdles, what they were. And the hardest part was that there was such a preconceived notion of what this customer wants to buy. It wasn’t about style, it was about function. 

YS: Did you find that price point and attitude to be kind of cynical? 
AC: 
There was this mantra that the plus-size customer was very budget sensitive; they don’t dress up. I knew I wasn’t that woman. I wanted to go to a party and know that no one else would be wearing my dress. It was kind of demoralizing to be in a culture where that wasn’t the established thought. There’s a lot of baggage in the industry. So I left the company in 2009 to launch the blog Madison Plus. 

Courtesy of Hey Gorgeous

YS: You ultimately had 100,000 uniques a month, which is huge. 
AC: 
There was a huge surge in plus size blogging at the time. Gabi Gregg and Nicolette Mason got their start around then as well, and Crystal Renn and Ashley Graham were starting to get headlines. At the same time, there was this huge disconnect. Retailers were saying, ‘We’ll take your money’ because the 2008 crash had left them looking for white space, for other revenue streams. But they didn’t want to really address the plus size woman herself. It was, ‘We’ll make a plus size line but we won’t put in on any floor in our department store.’ 

Related: How A Plus Size Girl Navigates the Pin-Thin World of Fashion

YS: Did you find that a lot of outlets didn’t really want this woman as their customer? 
AC: 
There were a lot of ways of sidestepping this woman, even though they knew this woman was 60% of the population. The constant pushback from the fashion industry was depressing. I had one meeting with a major department store when I was a blogger, and they were like ‘We really want to address this woman, but we don’t have any budget, so how can you help us?” 
I met my CEO Dave then, who said to me, ‘Why aren’t you selling these brands?’ It was a lightbulb moment, so then we launched the site for retail with Madison Select Plus. 

Courtesy of Hey Gorgeous

YS: When you shifted to Hey Gorgeous, was it in part to get away from the word ‘plus’? 
AC: 
I don’t mind being referred to as a plus woman but a lot of people do. It was a killer. So we rebranded to focus on fashion first. 

Related: How Shopping With Plus Size Model Denise Bidot Made Me Face My Own Body Issues

YS: Is there another word that’s better?
AC: 
If I had millions of dollars that would be the focus group of my life. It’s not romantic in any way, but when people ask who our clothes are for, I say it’s just the average woman. 

YS: You shoot on models who are a size 14. Do you get any grief from that, from larger women? 
AC: 
Yeah absolutely, I would love to shoot on more body types, but we’re a small team and we have to do what we know works right now and as we grow, our content will grow, so to those who wish we used larger models, I say be patient with me. 

Click below to see some of Cheshire’s favorite New Years Eve dresses from Hey Gorgeous