When March Madness rolls around, we all love to root for the Cinderella teams—the scrappy underdogs who defy the odds, take down giants, and capture the hearts of fans everywhere. These teams may not have the biggest budgets, the most elite recruits, or the highest rankings, but they have something even more powerful: strategy, heart, and an ability to seize the moment.

The same holds true in marketing. Some of the most iconic brands started as underdogs, doubted by competitors and consumers alike, only to rise to the top through smart positioning, strong storytelling, and a little bit of that Cinderella magic.

So, how can your brand pull off an upset? Let’s break it down.

What Makes a Cinderella Story?

Cinderella teams and successful underdog brands have a few things in common:

• They embrace what makes them different. Instead of trying to fit in, they lean into their unique strengths.
• They build passionate fan bases. People love a good story, and the best underdog brands create loyal communities around their mission.
• They take strategic risks. Without the luxury of massive budgets, they rely on creativity, agility, and timing to gain traction.
• They don’t listen to the doubters. Every Cinderella team has been underestimated, but that only fuels their drive to prove people wrong.

One of the best real-world examples? Crocs.

Underdog Brands That Beat the Odds: The Crocs Comeback

Few brands have experienced as dramatic a turnaround as Crocs—a story that hits close to home for me because, hey, they were founded right here in Broomfield, Colorado! Launched in the early 2000s, Crocs introduced a simple but polarizing product: a foam clog designed for comfort, not aesthetics.

At first, Crocs gained traction in niche markets—boaters, nurses, and chefs loved them for their comfort, durability, and functionality. But as the brand grew, so did the backlash. Fashion critics mocked the shoes. By the early 2010s, Crocs seemed destined to fade away, struggling with brand identity, declining sales, and over-expansion.

So how did they make a Cinderella comeback?

Leaning into the Hype (Even the Hate)

Instead of fighting the perception that Crocs were “ugly,” the brand embraced it. They turned irony into identity, making their unconventional look a selling point. Gen Z and Millennials, known for championing “ugly-cool” fashion, started to see Crocs as a statement piece rather than an embarrassment.

Strategic Influencer & Celebrity Endorsements

Crocs tapped into cultural credibility by collaborating with unexpected partners like Post Malone, Justin Bieber, and Balenciaga. These partnerships transformed Crocs from a punchline into a must-have item. Suddenly, what was once seen as out-of-style was now high fashion.

Limited-Edition Drops & Brand Collaborations

Taking a cue from sneaker culture, Crocs created scarcity and demand with exclusive colorways, high-profile collabs, and limited-edition collections. This not only kept the brand fresh but also drove urgency among buyers.

Owning the Comfort Narrative

Through all the reinvention, Crocs never abandoned their core value proposition: comfort. As consumers shifted toward casual and functional fashion (especially post-pandemic), Crocs was perfectly positioned to ride the wave.

The result? Over $3 billion in revenue by 2023 and a spot back in the mainstream. What was once written off as a fad became a global lifestyle brand.

The Cinderella Marketing Playbook: Strategies for Success

Want to pull off a marketing Cinderella story of your own? Here’s how:

1. Find Your Unique Angle

Cinderella teams play to their strengths, and underdog brands must do the same. What makes you different? Instead of blending in, own your distinctiveness.

2. Tell a Compelling Story

Fans don’t just love Cinderella teams for their performance—they love the story behind the journey. Your brand’s history, mission, and challenges make for a compelling narrative. Use it.

3. Leverage Guerrilla & Digital Marketing

Underdog brands don’t have Super Bowl ad budgets, but they use creativity and social media to get noticed. Think viral moments, influencer partnerships, and grassroots campaigns.

4. Engage & Activate Your Audience

Cinderella teams win because they have fans cheering them on. Turn customers into advocates by creating a brand community they want to be part of.

5. Stay Agile & Adapt

March Madness is unpredictable, and so is business. The brands that thrive are the ones willing to pivot, experiment, and take risks when opportunities arise.

Final Buzzer

Crocs could have disappeared into obscurity. Instead, they rebranded, embraced what made them different, and came back stronger than ever. The lesson? Underdog brands can win big—if they play their cards right.

So, what’s your brand’s Cinderella story? The next upset victory might just be yours.

Overtime: Does your business need help scoring points?

If your brand is facing its own underdog moment, I’d love to help you turn the page. Whether you need a sharper strategy, stronger storytelling, or a bold new direction, Wildwood Creative offers the fractional marketing support and creative insight to help you get there.

Let’s connect on LinkedIn or explore services at Wildwood Creative to see how we can rewrite your next chapter—together.