Why Kmart, Payless, and Forever 21 Failed—And What Every Beauty Entrepreneur Needs to Learn From It

Success leaves clues.

So does failure.

Some of the most recognizable brands in the world—Kmart, Payless, Forever 21—had massive success, loyal customers, and hundreds of stores. And yet… they still collapsed.

Not because they didn’t have great products or brand recognition.

But because they stopped adapting.

And that’s where the lesson is for all of us—especially beauty entrepreneurs.

If billion-dollar companies can fall by ignoring trends, refusing to pivot, or losing touch with their audience, it’s even more important that we pay attention to what went wrong… so we can build businesses that go the distance.

1. Kmart – The Brand That Forgot to Grow

Once the king of convenience, Kmart had more than 2,400 locations in its prime. Today, just a handful remain.

Why Kmart Failed:

• Ignored Innovation: While Walmart and Target upgraded their technology and supply chains, Kmart stayed stuck in the past.

• Outdated Identity: They lacked a clear brand story—weren’t the cheapest, trendiest, or most convenient.

• Poor In-Store Experience: Messy aisles, low inventory, and lack of customer service.

• Slow to E-Commerce: They waited too long to prioritize online shopping and delivery options.

What They Should’ve Done:

• Modernized their systems and invested in online ordering early

• Clarified their brand voice and customer promise

• Focused on experience and efficiency in-store

• Streamlined locations and improved top-performing stores

Esthetician Lesson:

Don’t rely on old systems. Upgrade your booking experience, get clear on your brand identity, and focus on delivering ease + excellence every time a client walks in.

2. Payless – Digital Denial

Payless was known for accessible, affordable shoes. But when the world went digital, they didn’t go with it—and it cost them everything.

Why Payless Failed:

• Delayed Online Shopping: While Zappos and Amazon were thriving, Payless stuck to storefronts.

• No Loyalty or Community Building: No email strategy, no rewards, no retention.

• Lack of Innovation: Store design, marketing, and inventory stayed static.

• Overexpansion: They kept opening stores instead of strengthening operations.

What They Should’ve Done:

• Built a mobile-friendly online store years earlier

• Launched customer retention strategies and clear brand messaging

• Prioritized fewer, better stores with stronger merchandising

• Partnered with influencers or launched niche campaigns

Esthetician Lesson:

If you’re not visible online, you’re invisible. Your booking link, online store, and client communication should all be optimized. And if you’re relying only on referrals or Instagram DMs—it’s time to level up.

3. Forever 21 – Too Fast, Too Generic

Forever 21 dominated the 2000s with fast fashion and massive stores—but it all came crashing down.

Why Forever 21 Failed:

• Expanded Without Insight: Opened stores globally without understanding climate, culture, or demand.

• Ignored Values Shift: As consumers cared more about sustainability, F21 stuck to mass production.

• Underestimated E-Commerce: Newer online-first brands outpaced them.

• No Clear Focus: Their stores were overwhelming, with no curated experience.

What They Should’ve Done:

• Curated smaller, boutique-style stores

• Introduced slow fashion or eco-conscious collections

• Invested in a stronger online presence and content strategy

• Focused on community, not just volume

Esthetician Lesson:

You don’t have to do more—you have to do it better. Don’t expand, launch, or scale without a strategy. Focus on what your audience wants now, and how you can deliver it better than anyone else.

So What Can You Learn From These Mistakes?

These companies didn’t fail because they weren’t good—they failed because they stopped evolving.

What NOT to Do:

• Don’t skip out on digital tools (booking, reminders, online sales)

• Don’t avoid raising prices as your demand increases

• Don’t serve “everyone”—the riches are in the niches

• Don’t wait for burnout before building systems

• Don’t assume what worked last year still works today

What TO Do:

• Stay flexible: The beauty industry changes fast—stay curious and open to trying new approaches.

• Use data: Track your rebookings, product sales, and client behaviors.

• Be memorable: Create a client experience that stands out and feels luxe.

• Grow with intention: Add services, offers, or staff only when the foundation is solid.

• Lead with value: Educate, connect, and serve—don’t just sell.

You don’t need a storefront in every city to succeed.

You need vision. Systems. Intention. And the willingness to adapt.

Learn from the rise and fall of giants. Build smarter, not harder.

And remember: you weren’t born to hustle forever—you were born to build something that lasts.