She started a comfy footwear brand for S’porean women that brings in S$1mil/year in revenue

Becoming an entrepreneur was never part of Cherriann (Cherri) Wong’s plans. As an “extremely risk averse” person who enjoys stability, she confessed that she’s always “longed to be a regular salaried employee.”

After graduating with a degree in Media Communications, Cherri went on to carve out a career in marketing within the travel and hospitality industry. For six years, she thrived in her role, while modelling on a freelance basis for local brands, a pursuit she had picked up during her university days.

It was during her modelling assignments that Cherri faced a recurring issue—she struggled to find shoes that met both her aesthetic and practical needs, and the more she searched, the more apparent it became that there was a glaring gap in the market.

Determined to address the issue, Cherri decided to take matters into her own hands by starting Sunday Staples in 2018. Her goal was simple: to create footwear that lets women move seamlessly from morning meetings to after-work plans, without the pain and discomfort that often comes from long hours on their feet.

I faced so many problems while looking for suitable shoes that I was less motivated by entrepreneur spirit than plain-old necessity [when starting up Sunday Staples].

Shoes were either too stiff, too painful, or always caused blisters, while the comfortable ones were often too expensive or too ‘aunty-looking’ for me.

Their first collection sold out in two weeks

Cherri’s brand struck a chord with customers almost immediately. According to Cherri, after she invested S$5,000 to launch her first collection—a single design in three colourways—it sold out within two weeks.

The brand’s momentum only grew from there—in just two months since its launch, she said that Sunday Staples had generated S$18,000 in sales, selling 500 pairs of shoes including backorders.

At first glance, some of Sunday Staples’ shoes might appear a little basic, but Cherri explained the approach behind their simplicity:

“Designs tend to be quite universal across brands, especially when it comes to trends. But what we do best at Sunday Staples is adapting these designs to better suit Singapore’s landscape.”

Sunday Staples’ shoes are crafted with softer soles, and the brand prioritises using “soft leather” to minimise blisters and abrasions.

“Unlike European shoes, which are designed for their varied terrains, which are often uneven and cobbled, our materials and designs cater to Singapore’s smooth pavements, malls, and roads. This allows us to swap out stiff soles for softer and more flexible ones,” Cherri explained.

As Singaporeans are usually on the move, Cherri shared that the brand strives to create shoes with lower, block heels as much as possible.

“Most of our heels are made with low block heels of about 1.5 inches, while our highest heels only go up to 2.5 inches, so it still elevates your look without sacrificing comfort.”

In addition to ensuring a comfortable fit, Sunday Staples also places great emphasis on designing footwear with flattering colour options that complement Asian skin tones.

The reality of scaling a business

After the initial surge of success, Cherri was driven to expand Sunday Staples’ offerings, and by 2021, she had successfully established three retail outlets for the brand.

However, she was quickly hit by the complexities of scaling a business, from managing hiring and logistics to ensuring timely deliveries.

Hiring local fashion designers turned out to be one of the most pressing challenges for the business—while the team now includes three full-time designers, it took years to source these talents.

Another significant challenge Cherri faced in her journey was finding good and reliable factories to produce her footwear. In the early stages of scaling production, Cherri realised that their factory could not keep up with the brand’s growth—it lacked the necessary resources and manpower.

The pandemic added another layer of complexity, making it nearly impossible to maintain the quality of their offerings without in-person factory visits.

As soon as air travel restrictions were lifted, Cherry flew to meet with larger, more established factories that were experienced in catering to international clients.

“We managed to secure agreements with several large factories who were adept at producing at the quality standards that we needed,” she shared. “Nothing beats going down and speaking to the managers face to face, and articulating our demands and requirements to them.” 

As a result, this not only reduced defects, but also ensured consistency across Sunday Staples’ product lines, leading to a more than 70% reduction in customer complaints, Cherri shared.

Today, Sunday Staples has implemented a strict and streamlined production process to ensure that its products are consistently of high-quality. The brand shares its product designs with potential factories to develop prototypes, which are then tested and evaluated by the in-house team in Singapore.

Factories are selected based on a combination of quality, pricing, and historical performance. To maintain high standards, factories with manufacturing defects face penalties, including exclusion from future projects or invitations.

Pivoting from a 9-to-5 job to entrepreneurship

Like many entrepreneurs, forging her own path in the footwear industry also meant that Cherri had to confront risks and uncertainties.

During the Phase 2 Heightened Alert amid the pandemic, malls were reopened, but footfall was relatively low given the restrictions. Since F&B establishments were not allowed to operate during this period, they were the only establishments eligible for government rental assistance, leaving retail businesses like Sunday Staples to cover the full rent on their own.

“We were losing over S$30,000 a month, and our footfall plummeted by over 80% compared to pre-COVID—we were losing money on a monthly basis,” she shared. In contrast, her 9-to-5 job provided her a predictable income with steady salary increments.

I would be able to calculate my affordability for a house, a car, or even a vacation. Running my own business offers no such solace, and I often wish I had that kind of predictability again.

Yet, despite these setbacks, Cherri’s determination didn’t waver. Driven by her mission to empower women to feel comfortable and confident, she remains committed to the growth and success of Sunday Staples.

To date, Sunday Staples has a total of four retail stores. The brand hit S$1 million in annual sales in 2022, and has sold over 200,000 pairs of shoes since its inception.

As part of its ongoing expansion, Sunday Staples is actively exploring opportunities to open new stores in Kuala Lumpur and Jakarta. Additionally, the brand is considering partnering with foreign distributors to extend its reach to other ASEAN countries.

Reflecting on the business’ achievements, Cherri admits that she is still “largely in disbelief.”

“Operating multiple retail stores and running a sizeable business can seem very intimidating,” she shared. “But if you break down each challenge and take it one step at a time, it becomes much more manageable.”

We took on every setback one step at a time, and I believe that as long as we don’t give up, we can make a huge difference in the market in 10 to 20 years time. 

Featured Image Credit: Sunday Staples/ Cherri Wong