One of the best things that happened to Gayla Bentley was when she broke her neck while delivering jewelry to a client’s husband, whom she had met at Saks Fifth Avenue. While injuries are never a thing to celebrate, if it hadn’t happened, she probably would have never gone to Paris, France. She wouldn’t have been able to send notes to the human resources department at Sakowitz, and her career would not have inspired an entire wave of people.
Similar to how a neck injury was crucial for Bentley’s career in the long run, Bentley’s career was crucial for the existence of plus size fashion, plus size acceptance, and confidence to be a plus size woman, proudly.
Bentley made waves when the water seemed to be forever still, but it was by no means easy for her. After years of working at Saks Fifth Avenue and being a pioneer to help bring in petite and larger sizes, she took a leap of faith to create the Gayla Bentley Fashion Design Group.
“I worked out of my home for three years, till I had it down, and then I had a huge fashion show. I would invite all the who’s who of Houston in the fashion industry to come to a private fashion show with all my designs, and I gave them all these small booklets to fill out, without putting their name on it, to score each outfit,” Bentley shared. “I could review all that to see if I had what would be needed to become a fashion designer, because it’s a very expensive business to get into, so you don’t want to just jump into it. And the results were resounding. Yes, yes, yes.”
Though her clothing brand had a rough start, she had the encouragement she needed. Due to her past experiences working as a Club Director at Saks Fifth Avenue and a previous business endeavor, Gayla Affairs Co-Tours, where she would plan trips abroad and shop with women in Europe, she had seen women’s bodies and heard their opinions for 20 years leading up to this moment.
Her first collection was inspired by her first business: Gayla Affairs Co-Tours. Though she noticed a lack of plus-size fashion in every realm, Bentley frequented an airport and plane due to her travels to France (with her business), so she created a travel collection. However, when she couldn’t find any comfortable clothing, she went a step further and created her own fabric.
Creating her own fabric was an investment because she could only buy it in bulk — but she knew that the industry needed this, and if no one else was willing to make the sacrifice, then she was.
The encouragement from friends and family was crucial to her success, but securing the funding she required proved nearly impossible. Still, if anyone could accomplish it, Gayla Bentley could.
“I did find money, but it was like finding water in the desert. We [she and her husband] went through all of our money. I sacrificed everything. I never took a paycheck, which now I realize was not a very smart thing to not to do, because now that I’m 20 years later, my Social Security is not what it should be, because I didn’t take a paycheck. I kept putting the money back into the business.” Bentley shared.
Creating and owning a fashion brand is not cheap, but Bentley began her company in 2001, when there were very minimal plus size options for designers. Creating fabrics and pieces got very expensive, very quickly.
Eight years later, in 2009, things were still difficult for plus size fashionistas everywhere. However, Bentley got a call from a group of producers for a new show at the time, called “Shark Tank.”
Bentley had been receiving good press at the time, so she thought, why not? She understood that the industry was still far from where it needed to be, and this could be a big help. After pitching her brand, the Gayla Bentley Design Fashion Design Group, to a panel of investors, aka Sharks, including Kevin Harrington, Daymond John, Kevin O’Leary, Barbara Corcoran, and Robert Herjavec, two investors agreed to go in on a deal.
In the episode, Bentley went in seeking $250,000 for 20% equity, but left with a deal of $250,000 from Corcoran and John both for 50% equity. Corcoran knew as a woman how necessary this brand was, while John already had a fashion line at the time, bringing in a great deal of experience.
After the show aired, Bentley was the number one Googled person for 24 hours and received an overwhelming amount of support, including her largest order ever. A department store placed an order with the Gayla Bentley Fashion Design Group for $1,000,000.
The high of success post-Shark Tank was everything.
“Barbara was wonderful. She gave me a brand new penthouse in New York City to show my collection on QVC. This beautiful penthouse overlooks the city, and it snowed that night, so everything looks so magical. All this money you have to keep up with, you fly your staff up there, and QVC calls the last minute, says they’re not coming because of the weather.” Bentley shared.
Being let down was not abnormal for this line of work, as unfortunate as it was. Nobody was cheerleading for a plus size clothing line or celebrating plus size individuals in general, yet Bentley persevered.
Corcoran and John’s involvement with the Gayla Bentley Fashion Design Group lasted six months, as the deal was never fully signed. Bentley then found a way to finally make her clothing more affordable, which was something she aimed to do.
She knew it was hard enough to find plus size fashion, so she wanted to make sure that people could afford it. Unfortunately, the gentleman who promised her more affordable clothing manufacturing lied. On top of that, he stole all of her money.
“And my husband said, ‘We have to close, I mean, we just have to’,” Bentley said. “I just cried and cried and cried for weeks and weeks and weeks. Then, I pulled myself back up and went and worked with felons… from fashion to felons… because I had to go do something that could help me with my pain.”
A clothing brand had been Bentley’s dream for her entire career. Being able to serve fellow plus size women and help them find beautiful pieces of clothing as well as their own style, was the plan. But just because the end of her clothing brand came as an unexpected and unwanted twist does not mean that her work did not make an impact.
Gayla Bentley is one of many pioneers who hoisted the plus size industry onto their backs and ran with it.
“In addition to Gayla, there’s other women, Gwen DeVoe, Susan Moses, Madeline Jones, Sharon Quinn; these women were inspirations. They motivated me to be audacious and create the media that I didn’t see, to be able to create, and to do the things. They were unapologetic, they were audacious, they were bold, they were exciting.” Marie Denee, Editor-In-Chief of The Curvy Fashionista, said.
It takes a village to encourage a change, to initiate a movement, but Bentley’s work is not done — even after her clothing brand officially closed in 2024. Though her fashion brand has been a large portion of her life, she has had other important experiences that have made her into the fashionista she is today.
“I remember seeing Gayla Bentley on Oprah as a little girl. As a girl who was always on the thicker side, seeing her being successful and happy in her own skin was a culture shock,” Kerbi Rucker-Louis, the Managing Editor at The Curvy Fashionista, shared. “As I grew up and faced those times when I felt insecure about my body or weight, I remembered her.”
Gayla Bentley Releases Her Memoir
Fashion’s Stepsister: A Journey to Style, Bentley’s memoir, was released in September 2024. While the book touches on her career, it also touches on her childhood and her adolescent years.
From having the nickname “chubette,” to having to wear a caftan to her prom because nothing else would fit her, she went through it all.
“I can look back on my whole life and have no regrets and have no major bruising from all of that either, because God has helped me to heal from all that,” Bentley said. “I cried so much when I was younger because I couldn’t understand how I couldn’t figure out how to be pretty.”
Growing up, she would babysit during her free time. While doing so, she found a copy of Playboy Magazine, and after the kids had gone to sleep, she began to flip through the magazine. She began to compare her body to those she saw in Playboy, realizing that maybe a funny personality was not enough to attract a boyfriend.
Similar to many girls who grow up plus or curvy, Bentley struggled to find age-appropriate clothing that also fit her. She would go to Lane Bryant, but it didn’t make sense for her, 12 years old at the time, to be wearing the same blouses she saw her grandmother wearing.
“It was in the dressing room at that time that I really heard God say to me, ‘Don’t worry, you’re going to learn how to dress yourself and dress other women,’ and that’s when it all started,” Bentley said.
Her trials growing up became some of her greatest strengths, as they taught her how to work in an environment that wanted the opposite of what and who she was.
In the memoir, Bentley goes into detail about a prom prank that was played on her. Kids joked that the hot guy wanted to go to prom with her, and as every girl dreams, she also dreamt it to be true, only for laughs to be thrown her way.
Looking back on it, she said, “It makes me appreciate who I am today so much more that I had to go through all of that, even though it didn’t feel that way when I was going through it.”
Gayla Bentley has always been a pioneer. Even though she was pranked and not favored in school, she became the first female president of her high school class because, at the end of the day, people believed in her.
People believing in Bentley was important in every business endeavor she had from that point going forward. After she went to college and met her roommate and fashion inspiration, Nina Sammartino, she began Gayla Affairs. With this business, her styling clients consisted of professors and medical personnel.
This styling taught her so much as she was still learning who she was and what she wanted to do (like every other college student). Shortly after her college career came to an end, was when she began her European travels, where she would soon begin the Gayla Affairs Co-Tours, and send notes to the Human Resources department at Sakowitz of what European fashion looked like. Those letters ended up getting her a job at the renowned luxury department store.
Even that wasn’t easy. Bentley relied on public transportation to get her to and from work, since she didn’t have a car, and Texas is not necessarily known for having great public transportation. She only had $144 to her name when she came back for this job, but since her days in the dressing room, she has known that she was meant to help other women.
Her first client at Sakowitz was Her Majesty, Queen Noor of Jordan, and when she calculated her sales from her first day, they totaled $36,000. The following day, Bentley was promoted to Director of Personal Shoppers.
Bentley has always been full of determination and grit, and she isn’t slowing down. In her memoir, she gives tips on how to style and dress for every kind of woman, because before she had access to the clothing she actually wanted to wear, she had to learn those rules, too.
Plus size fashion has come a tremendous way from where it was when she began her journey, but it is by no means at its finish line.
“A lot of what I think is missing [from the plus-size fashion industry] is investment, because you have the creativity, you have the ideas, you have the visions. But in order for it to be properly executed, you need, like financial investment,” Marie shared.
Investment was what Gayla needed terribly, but it was never properly given. Though there are more online clothing options today, there are still very few brick-and-mortar options.
The plus size community, fashion aside, is going through a lot with the rise of weight loss medication, but in reality, this community has always gone through a lot. It takes people with the audacity to happily take up space and create chairs at a table that has never invited them, and for this community, that person is Bentley.
“Being a plus sized woman is a political statement in and of itself, daring to show up as a plus size woman, to confidently take up space is a political statement. Being a plus sized woman wearing clothes that go against ‘the rules’ is a political statement,” Marie shared.
Being a plus-size woman with a fashionable sense can be an obstacle, but to be a plus size woman with style is not, thanks to Gayla Bentley.
Who is your favorite plus size fashion pioneer? Share in the comments!
