Lloyd Boston Takes on Chief Creative Officer Role at Ashley Stewart as Brand Accelerates

Lisa Lockwood
·8 min read

Ashley Stewart is making headway under new chief executive officer Gary Sheinbaum.

Sheinbaum, the former CEO of Tommy Hilfiger Americas, came on board in January and the next month appointed Lloyd Boston chief creative officer. Boston runs his own business and is a style contributor and correspondent for “Wendy Williams Show,” and a regular contributor and style editor to NBC’s “Today” show and ABC’s “The View.” He’s also an author, red carpet authority, content creator and branding executive.

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At Ashley Stewart, Boston will be responsible for all things creative, from the way in which the retailer of apparel, intimates and accessories for women sizes 10 to 36 is positioned to how the product shows up visually in-store and online, to fashion shoots, ad campaigns and conceptualizing a new store of the future.

Founded in 1991, Ashley Stewart has 83 stores across the U.S. as well as e-commerce. The plus-size brand has made a comeback after filing for bankruptcy in 2010 and 2014. Today, Ashley Stewart is owned by Monroe Capital, a Chicago-based asset management firm.

In an interview, Boston, 50, said the job came about organically.

“Gary and I go way back to the Tommy days back in the ’90s,” said Boston, recalling his days as vice president, art director at Hilfiger. Boston said he heard that Sheinbaum was pivoting after 25 years to Ashley Stewart and told him that he was looking to do a reentry after 20 years under his own shingle.

“It’s got to be the right place. I did not want to be at just another sausage factory of a fashion house. I wanted to be somewhere that just made sense, and this really makes sense,” said Boston.

In his creative role, Boston won’t be designing the collection, but will be working with the design team. Earlier in his career, Boston worked in the plus-size space at Jones New York and was the face of the brand for seven years. “We had a huge Woman division as they called it [and I was] helping on the inside and connecting to women of all sizes,” said Boston.

Boston said he’s looking forward to the opportunity to work in the plus-size arena.

“I love the fact that this brand is very unique in that the audience has been underserved for years and found a special place at Ashley. When you walk into the Ashley stores, it’s like you’re almost walking into a club. The salespeople know the customers by first name, they’re in the dressing room and almost having these little parties, where they’re trying things on and high-fiving and giving each other style tips. All the stuff I’ve been doing on TV for years,” he said.

Boston said what the brand needs is bigger amplification. “Someone who’s worked as a fashion editor and comes in and really homes in on what women hopefully will be drawn to. I’m just looking at this collection and saying, ‘Why aren’t we talking about this coat more?’ ‘This is a pant that we should be doing every season.’ It’s when you find the diamonds in the rough. Oftentimes, when you’re too close to something, you just don’t see the beauty of it, you’re just moving on to the next trend,” he said. “You and I know that when we see the runways, they’re not trends until they hit the streets,” he said.

Boston said he’s loving the fact that he can look around at what Ashley Stewart’s done to create their own trends, as well as redefine some of their classics, and put those things out ahead of market.

One thing he knows for sure is that Ashley Stewart customers like their fashion denim. “It is bolder and brazen and destroyed and destructed and acid washed and embellished, and really speaks to what’s happening with plus-size women. Women are empowered to celebrate their curves, versus the market saying, ‘let’s just put them in core denim, as long as it fits,'” he said. “Ashley’s fashion denim is, ‘Come on, we’re going to the club, we’re going to Miami, we’re going to a photo shoot. She is ready with the trends,” he said.

Ath-leisure is another important category, and Boston said the retailer just did a partnership with Fila Curves that was a huge success and will continue. Special occasion dressing is also significant.

Boston said the brand is positioned at the “mass-tige” level. He equated it to brands like H&M, Uniqlo, and Zara, where one finds the trend that’s in the best fabric at a value price.

According to Boston, over the last 30 years, Ashley Stewart’s “secret sauce” has been that the brand has been known for color and bold prints and interesting trends right off the runway, such as a peplum or a cold shoulder. “Things that many designers wouldn’t offer to a woman of curves,” he said.

“Ashley was bold enough to say, ‘we’re going to double down on these trends, and give them to you whether you’re a size 12 or 22. We’re going to give it to you in a way that fits, flatters and forgives.’ We’re just not going to dip you in the hottest trends because they’re hot.…There’s more thoughtfulness going into the designs. That’s the part that I like.”

Boston’s new role is a full time gig, although he said Sheinbaum has allowed him to continue with things connected to his Lloyd Boston brand, such as covering red carpets on both coasts for “The Wendy Show,” and other TV shows. “With that I hope to be able to bring that information back to Ashley so we can be ahead of the curve. If I’m on the red carpet, instead of just popping up on TV and critiquing it, I want to bring those trends into our design area and into our creative area. I don’t have to completely turn out the lights to Lloyd Boston, I can just dim them.”

Asked if he’ll be making personal appearances on behalf of the brand, he said he would, when it makes sense to be consumer-facing. “I really want to dig in, almost be in that cocoon for a few months, and get the brand where the word of mouth is even bigger than it already is. I don’t have an ego. If I don’t have the right influence to speak to the audience of consumer facing, I think it’s best for me to find the people who are doing that, maybe it’s a celebrity and maybe it’s an influencer. I’m happy being behind the scenes,” he said.

Boston said they are also working on Curvy Girl by Ashley Stewart, which speaks to a younger woman. “Ashley is ageless. The Ashley customer will dip into the Curvy Girl selection as well,” he said. She may wear Ashley Stewart to work, but may want Curvy Girls for a trip to the islands.

Boston, who was born and raised in New Brunswick, N.J., plans to go back and forth between Secaucus, N.J., where Ashley Stewart is based, and Los Angeles, where he has a home. Last week was his first official week in the New Jersey office.

Sheinbaum explained that through their market research he has found that with the Ashley Stewart customer, it’s much more than just selling her clothes. It’s about a cultural connection, establishing a relationship, and the experience.

“The amazing thing about Lloyd is he has this incredibly diverse, versatile background. He’s got a background in retail, in fashion, in product design, he’s an artist, a graphic artist, he’s also a businessman and a brand strategy guy, and he’s also written books and has been on camera. It just makes him so qualified to kind of bring this quality product and authentic storytelling which is a big part of my vision,” said Sheinbaum.

He said Boston will be working on all things creative. “He really is an expert in helping us communicate the brand voice. His ability to creatively tell stories and show women how to wear it and how to work it There are so many ways he’s going to contribute and help us grow this business,” said Sheinbaum.

In addition to elevating and upgrading its product, Sheinbaum said they’re working with other brands, such as Fila, Champion and Lala Anthony, and are just about to bring DKNY on board.

Looking ahead three to five years, Sheinbaum said they will consider wholesaling the line. “When we do all the things we’re working on and really feel so good about our product and our position, then I would start to think about wholesale,” said Sheinbaum.

The web is a major priority and “is doing very well,” he said.

“All the KPIs are up. Our big challenge is to get new customers. We’ve put in place virtual stylists to help maximize the e-commerce business. We’re building the team as well as the capabilities, functionality, speed, and shopping experience, and Lloyd will play a big role in that as well,” said Sheinbaum.

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