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By Anastasia Mills Healy

Design by Justin Negard

In August, Cracker Barrel made national headlines when it unveiled its new logo, hoping to breathe new life into a business that faced stagnated growth and a 40 percent drop in stock prices the previous year. Gone was the iconic image of an older man sitting in a wooden chair leaning against a barrel. Even the phrase “Old Country Store” neatly printed across the bottom was removed. In its place was a new barrel-shaped logo in a similar, brighter gold with “Cracker Barrel” written in a similar font. It was clean; it was modern; it was fresh; customers hated it. Stock prices dropped even further, and customers described the logo as  “generic,” “soulless” and “bland” on social media. Eight days later, Cracker Barrel brought its former logo back.

Individuals, products and companies use branding to communicate who they are and what they stand for. But branding doesn’t stop with a logo. “The logo is part of branding; it’s a symbol of a brand,” says Floyd Rappy, president of Studio Rappy. “It’s really important, but it can’t do all the heavy lifting in projecting what a company is about. Branding is a promise.”

And creating that promise is a process. Whether you own an artisanal cheese shop, are a high school teacher or you are planning a nonprofit gala, branding is essential.

Cracker Barrel’s old logo and new logo side by side.

Understanding branding

Rappy gives the example of walking into a Starbucks in London. “There’s an expectation about what will be on the menu and what it will look like. There’s a promise of familiarity and quality.”

Yet the visual identity is also critical. “You should have a visual voice in how you present your product, yourself and your company,” says John DeFrancesco, an independent graphic artist and branding expert. “You are so passionate about what you’re doing, and you should be equally as passionate about how you’re going to deliver that to your audience.”

For the artisanal food shop owner, high school teacher and nonprofit gala planner, once they have defined their personality and determined their target demographic, they can begin to create a visual identity.

“For a small business, visual brand consistency is key, especially if customers can see your logo or color consistently when using your product,” says DeFrancesco. “It’s a reminder of where they made the purchase.”

Teachers should apply their visual identity to all materials, including PowerPoint slides, handouts, digital assignments, etc., and the same colors, fonts and style should also be reflected in their classroom decor. These details set the tone for the class.

And if you’re planning a gala, the nonprofit probably has a solid visual identity you can work from. DeFrancesco says you are selling consistency, and your message is key. You want your target demographic to connect the sign they pass in the car to the emails you send and your social media posts.

Rappy, who studied at the School of Visual Arts with design legend Milton Glaser, says Glaser explained that design, along with branding, must be intentional. “He said it’s used to solve a problem,” says Rappy. “We have to know what the problem or challenge is and identify the goal. Once we know that, we get to work figuring out the intention. Then everything else falls into place: color, typography, attitude, photography, voice, language. This is what design is in its highest form—it’s solving problems, getting to the root of the intention, and resolving that.”

Determining the problem will, of course, vary. For example, the small business might struggle to stand out among the competition. The teacher could find it challenging to hold their students’ attention. And the event planner may actually face the problem of competing events on the same night. Branding can help solve these problems.

The psychology of branding

“So much of what we do integrates psychology,” Rappy says, referring to how branding helps businesses/organizations communicate their message. Similar to how a group of people studying a painting may have different reactions, branding “is modified in the mind of each viewer,” Rappy explains. Branding experts apply psychological principles to understand and influence consumer behavior. They help shape the brand’s perception and create an emotional connection through visual cues, storytelling and brand personality. These psychological principles help the company project its value proposition which, in turn, builds loyalty and drives decisions.

Companies spend enormous amounts of time and resources on branding, including market research, focus groups and developing a brand identity, but “at the end of the day, a brand is what a customer thinks of it; it’s a feeling about a company,” Rappy says.

Would the artisanal cheese shop want customers to chuckle at their sense of humor when they see the playful mouse logo, or do they want the logo of a gentleman with a monocle and top hat to communicate they’re running a high-end shop? Similarly, does the high school teacher want her brightly colored classroom to reflect her big personality or let more muted tones speak to the seriousness of the topic they teach? And when it comes to a nonprofit gala, think of those ASPCA commercials featuring Sarah McLachlan’s song “Angel” and those sad puppy dog eyes. What emotions does that evoke? How can you evoke the right emotions and inspire the community to attend?

Keep it simple and consistent

Like Apple, “many of the brands that work, work because they’re so simple,” Rappy says. The artisanal cheese shop probably shouldn’t flood its Instagram feed with constant messages about sales and complicated or messy visuals; instead, it should focus on simple messaging, using set typefaces and colors, along with its logo to reflect its personality to draw people in.

The evolution of Apple’s logo.

“In a teaching environment, it becomes about staying on-message—both literally and visually,” DeFrancesco explains. “Uncluttered and focused visuals will inspire an open environment that welcomes learning.”

And the gala messaging will have more impact if the branding is in line with the visual identity of the nonprofit. Yes, the evening’s theme can stand on its own, but it should tie back to the visual identity people know and respect. For example, keep the shade of blue in the logo, and try to match the typeface style. These small branding details help consumers maintain that same emotional connection many already feel towards the nonprofit. “Stay on message,” says DeFrancesco. “Be sure your vision delivers to your target. It’s okay to infuse creativity into new executions, but be sure you are on the same visual page and your image is front and center.”

Three Newbie Branding Mistakes

1. Scalability.

Will a logo hold up when it’s scaled way down to the little logo on Instagram or a mobile device?

2. Logo clutter.

Is your logo a strong, refined symbol of your business, or is it too literal, too ornate (multiple flowers or intricate lines) or showing too much? That will interfere with scalability and usability in a range of applications.

3. Typography fussiness.

Readability at a glance is important. Try to avoid ornate or trendy fonts.

Source: Floyd Rappy

Rebranding 101

While Cracker Barrel missed the mark, both experts agreed the brand needed a refresh. “Cracker Barrel is old, the logo was old, and their restaurants looked old,” says Rappy. “They were primed for a rebrand. The agency that did it retained the color and refined the type while keeping the ligature—the C and the B. But the logo had what we call brand equity, and people had an emotional connection to it.”

“I liked the new logo; I liked that they got rid of the old man,” DeFrancesco says. “I was recently in the Midwest, and it’s a different mentality. That old stuff is a comfort. Change is a difficult thing for some people.”

If you’re considering a rebrand, slow and steady is the way to go. “There’s a reason why old brands take a long time to change,” Rappy says. “If you Google the logo of Tide, today’s logo looks very different than the original, but nobody really noticed the changes along the way because they were subtle. People don’t like to see radical change in the product.”

Legacy brands should always change with the times, but the pacing of that change matters. Doing it too quickly can be jarring for loyal customers. “People don’t mind when things change and they don’t know it,” DeFrancesco explains. “Even the McDonald’s logo has changed over the years.”

How to work with a branding expert

“Computers have made it so easy for anyone to think they’re a designer,” DeFrancesco says. “It’s usually very obvious when someone uses Canva.” For some, like teachers or a personal brand, that’s probably okay. But for most, a branding expert can transform a business.

In his 30 years of experience, Rappy says he gets approached for three main reasons: to stand out, to look professional and  to reflect who they are. DeFrancesco likens developing a visual voice to creating a vision board when renovating or decorating a home. He recommends collecting photos and other representations of things you like—even if they’re not related to your business—to help the artist or art director.

“There are a lot of cheap ways to get a logo done,” Rappy says. “Do you value what we’re doing for you? If not, you should spend $500 for a logo from Fiverr.” But there’s so much more to branding than a logo. “You don’t know what you don’t know,” he cautions. DeFrancesco says a good designer does a lot more than what most people might realize, including the following:

  • Guaranteeing brand consistency for everything from labeling and packaging to web design.
  • Establishing brand guidelines for photography and copywriting.
  • Carefully choosing the right weight and color of materials for items like signs, banners and invitations.
  • Going “on press”—physically being present as materials are printed to ensure quality control for components like color and alignment.
  • Overseeing the visual identity of a company’s events.

“What you’re really looking for is someone who is aligned with you from a vision and budget standpoint,” DeFrancesco explains. Rappy adds, “Working with a design agency is a collaborative process. It’s about getting to the core of who you are. They will help you determine your mission statement, value proposition and why you are even doing this.”

And make sure everyone is on the same page, and in the same meeting, from the beginning. Rappy shared a story about a time when an entire team at his firm and the client’s marketing team worked together on a new branding strategy, but “after three months of work, the CEO finally focused on it and took everything in a different direction.” 

Executing your new branding

“Social media can feel overwhelming,” DeFrancesco says. “There are so many outlets, and you really have to take advantage of them all.” He had a small business client who resisted social media but experienced “a really serious bump in his business” after hiring a social media manager. However, this same business owner hired someone who didn’t follow brand guidelines when creating the storefront sign, resulting in a visual disconnect from his packaging, advertising and other branding. “Small businesses are dependent on the person at the top. If something falls flat, it’s because the person at the top isn’t properly managing that vision,” he says.

At the end of the day, “It’s about reaching out to an audience that wants your product or service,” DeFrancesco says. “It’s about executing your vision or inspiring the end user so they’re able to follow what you’re thinking.”

Rappy says if you are thinking about how to create your brand, you should reflect on a fundamental question: “What is your promise?” And then, make sure to deliver.

This article was published in the November/December 2025 edition of Connect to Northern Westchester.

Anastasia Mills
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A former editor at Condé Nast Traveler, Fodor’s, and Travel Agent, Anastasia Mills Healy is a Greenwich-based writer and editor who writes for Time Out, Lonely Planet and others, and is the author of “100 Things to Do in Connecticut Before You Die” and “Secret Connecticut.” 

Creative Director at Connect to Northern Westchester |  + posts

Justin is an award-winning designer and photographer. He was the owner and creative director at Future Boy Design, producing work for clients such as National Parks Service, Vintage Cinemas, The Tarrytown Music Hall, and others. His work has appeared in Bloomberg TV, South by Southwest (SXSW), Edible Magazine, Westchester Magazine, Refinery 29, the Art Directors Club, AIGA and more.

Justin is a two-time winner of the International Design Awards, American Photography and Latin America Fotografia. Vice News has called Justin Negard as “one of the best artists working today.”

He is the author of two books, On Design, which discusses principles and the business of design, and Bogotà which is a photographic journey through the Colombian capital.

Additionally, Justin has served as Creative Director at CityMouse Inc., an NYC-based design firm which provides accessible design for people with disabilities, and has been awarded by the City of New York, MIT Media Lab and South By Southwest.

He lives in Katonah with his wonderfully patient wife, son and daughter.