Anya Cheng, founder of, shares insights on empowering confidence through sustainable style in an interview with The Worlds Times. Cheng discusses Taelor’s mission to boost confidence by offering personalized styling services, catering to individual needs in various scenarios like job interviews and dating. The company’s clothing rental subscription model, coupled with AI-driven personalization, aims to extend the life cycle of garments, contributing to sustainability. Cheng emphasizes the importance of personal confidence in successful interactions and connections, highlighting Taelor’s focus on helping customers express their best selves without constant shopping. Additionally, she discusses strategies for promoting sustainability while prioritizing customer satisfaction, ensuring a positive and inclusive environment for both customers and team members. Cheng concludes by addressing competition in the sustainable fashion market, emphasizing Taelor’s unique value proposition of personalization at scale and its commitment to driving innovation and sustainability in the industry.

Transforming Confidence

We started the interview by asking, “Can you share an experience where you helped someone feel more confident in their appearance? How did you go about achieving this?”

Anya Cheng replied, “One of the experiences that stands out to me involves a customer who was about to attend a significant job interview. He was a recent graduate in North Carolina, transitioning from a more casual work environment to a corporate setting and felt quite uncertain about making the right impression with his attire. With his stylist’s help, he eventually got a job as a Data Scientist for a big tech firm in the Bay Area.

Another common situation where people need help to feel more confident in their appearance is dating. A study by Banana Republic indicates that 67% of daters experience stress over their date outfits, and studies including Social Psychological and Personality Science shows well-dressed daters receive 27% more likes and messages. Danny is an example — we helped him to get his dating outfits which he used for his dating profile photo-shoot. And he successfully got a date!

This is a common concern among many people, and it’s precisely where Taelor shines by offering personalized styling services that cater to individual needs. How does Taelor’s man’s clothing rental subscription work? It starts when customers sign up and complete a style quiz, which helps Taelor’s professional human stylists and AI to curate a personalized selection of clothes based on the customer’s size, style preferences, and upcoming events. The clothes clean and ready to wear are then shipped directly to the customer. They can wear these items for weeks and choose to either return or buy them at discount. After returning the items, customers receive a new shipment, keeping their wardrobe fresh and updated. Because it’s a rental model, most customers ended up trying something new and discovered their new style and became more confident after the transformation.”

Fostering Connections

The Worlds Times: How do you believe personal confidence contributes to successful interactions and connections with others?

Anya Cheng replied, “Personal confidence plays a pivotal role in shaping successful interactions and connections with others. It’s like the silent language of self-assurance that speaks volumes before you even utter a word. When we ask what impressions customers want to give out when wearing Taelor clothes, they often say, “fit, put together, professional, with style and clean”, instead of “fashionable.” People feel ready for their week because they look good but not “over the top ” or “trying too hard”, and that’s exactly what Taelor’s human stylist and AI are aiming for. At Taelor, we want our customers to be the best version of them.”

Unlocking Benefits

The Worlds Times: In what ways do you think sustainable fashion can positively impact both individuals and the environment?

Anya Cheng replied, “Sustainable fashion represents a critical shift in how we produce, consume, and think about clothing. Its positive impacts span environmental, economic, and social dimensions, benefiting not just our planet but also individuals and communities. Some of our customers tell us that knowing they aren’t just creating waste with clothes and still looking better make them feel good.

At Taelor, our model allows every garment to complete a full and meaningful life cycle — each garment was rented multiple times and when people buy them, it’s like-new pre-owned items. Also, our unique and rich data help fashion companies craft only what people truly desire. Our data is unique because with the rental membership model, we know people’s true preference unimpacted by the purchase price of the item — like how you decide what to watch on Netflix. We also work with eco-friendly brands such as brands that are made by recycled coffee ground, recycled plastic buttons, buttons that are made by cocona and more.

The current business model in the apparel brand/retailer industry is broken. It has been difficult for fashion brands to predict and test demand for new styles and markets with no fast, easy way to test products and get consumer feedback. In addition, it’s hard for menswear brands to acquire new customers or enter new markets because most men buy the same brands again and again. Current go-to-market channels are ineffective. As the result, they create a lot of waste due to excess inventory — 30% of clothes go directly from factory to landfill. Brands and retailers know circular fashion is a growing segment — 23% CAGR, $77B market — but not sure how to start.

And Taelor helps them to test the circular fashion model instantly by offering a two-sided circular platform — fashion brands and retailers send us their latest collection or excess inventory to Taelor, AI and human stylists pick the perfect items to help customers to get ready for their week, consumers then provide fast and unique feedback back to the fashion brands, and fashion brands acquire a new customer and use the unique insights to create the next collection. Brands test new products, monetize unsold inventory, get fast insights, and find new customers; customers discover new brands and styles and get pre-owned items at discount without the hassle of shopping. Together, we extend the life of garments and save the environment.”

Keeping a Finger on the Pulse

The Worlds Times: How do you stay updated on trends in sustainable fashion, and how would you incorporate this knowledge into your role at

Anya Cheng replied, “Staying updated on trends in sustainable fashion involves a multifaceted approach that includes continuous learning, industry engagement, and leveraging technology. We work closely with over 300 fashion bands. We also learn the latest insights from our strategic investors who are the manufacturers of leading brands including Lulu lemon, Nike, Hugo Boss and Uniqlo, as well as the Board Member of a circular economic foundation. We are active in the startup space where the latest sustainable practice, model and technology are borned.

We are not just staying updated on trend. We are also a trend-setter. Our unique data on how many times each garment can be washed and worn allow us to discover insights and trends by leverage AI and technology. As the founder of Taelor, incorporating this knowledge into our service is critical for ensuring that we not only offer stylish and relevant options to our customers but also uphold our commitment to sustainability.”

Creative Solutions for Garment Longevity

The Worlds Times: Describe a time when you had to creatively extend the life of a garment. What was the outcome, and what did you learn from the experience?

Anya Cheng replied, “The entire business is built on extending the life of garments. Our unique model encourages brands to produce garments with a long lasting lifecycle (slow fashion) and each garment’s life is extended as it gets rented among multiple people, which are both good for the environment. We use modern technology to clean the clothes that last long and carefully inspect each item that comes back to us and make sure they meet our standard before renting them out again.”

Fostering Sustainable Confidence

The Worlds Times: What strategies would you employ to promote the values of and encourage customers to embrace their best selves without constant shopping?

Anya Cheng replied, “We promote the values of by helping customers to shine in the situations they are going to have in the coming weeks. When our stylists curate outfits for our customers, we don’t just think about what five items in the shipment is what they will like most. Instead, we think about what mix and match they can do to have three completed outfits that would help them get ready for their upcoming weeks and also make them feel good.

Our variety of high quality items and rental model allows each item of clothing to be worn multiple times by various people, allowing each customer to discover and embrace their own style without contributing to overconsumption. Furthermore, when a customer finds a piece they truly connect to, they have the option to buy the like-new, second hand clothes and continue wearing them for years to come.”

Customer Dissatisfaction Resolution

The Worlds Times: How would you approach a situation where a customer expresses dissatisfaction with their appearance despite wearing products?

Anya Cheng replied, “Handling a situation where a customer expresses dissatisfaction with their appearance, despite wearing products, requires empathy, active listening, and a personalized approach to address their concerns. Our experienced customer service lead was the head of customer service at eBay. We review every single customer feedback at our executive meeting weekly and aim to make every customer experience perfect.

Our rental subscription based model allows customers to wear a variety of items, sending back any items that they don’t wish to purchase. There are five items in each shipment, and if one item does not fit, customers can still wear the other four items for weeks and return the shipment to get the next one. Before getting the next shipment, customers can tell their personal stylists their feedback which will be used to curate their next shipment better.

If a customer is deeply unsatisfied, they can always call customer service, but our AI also learns from each customer’s preference patterns over time (very quickly in weeks!) in order to curate a selection that becomes increasingly aligned to users preferences as they use the service more frequently. This trait of the service is designed specifically to decrease instances of customer dissatisfaction as they use more often.”

Anya Cheng’s Previous Endeavors

The Worlds Times: Can you provide examples of initiatives or projects you’ve been involved in that align with promoting confidence-building or sustainability in your previous roles?

Anya Cheng replied, “I have been an advocate for a decade for people who are in search of career excellence to leverage their strengths to build confidence and perseverance during difficult times, including giving TED Talks twice and writing two best-selling books. I use my personal job-searching stories on how to land a job after graduate school during the Great Recession by using what I know — I was a reporter before graduate school. I waited for hiring managers outside of buildings, got free conference tickets for networking by volunteering myself to write blogs for them, and found executives of big companies by simply having their names. I have a passion for sharing to inspire people and helping them discover what they can do.

My co-founder Phoebe Tan is a long-term advocate for sustainability. She is a frequent speaker in circular fashion and sustainability conferences. Taelor’s investor Sean Chao is a Board Member of a circular economic foundation. Taelor also sources sustainable brands including clothing items that are made from recycled plastic bottles and recycled coffee grounds.”

Balancing Customer Satisfaction

The Worlds Times: How do you prioritize customer satisfaction while also considering the environmental impact of the products or services you offer?

Anya Cheng replied, “Prioritizing customer satisfaction while also considering the environmental impact of products or services, especially in the context of, involves a delicate balance between delivering high-quality, personalized fashion experiences and adhering to sustainable practices. We strive to select clothes that have high quality and durability over quantity. The math is simple to us: if a garment can be rented out many more times, we don’t need to buy as much. Implementing a rental model significantly reduces the demand for new garment production and the associated environmental footprint. We also provide unique and rich feedback to our fashion brand suppliers to help them to create the next collection that’s in line with consumers’ preference so that there will be less waste.”

Personal Style as a Form of Self-Expression

The Worlds Times: Share your thoughts on the relationship between personal style and self-expression. How does this relate to’s mission?

Anya Cheng replied, “The relationship between personal style and self-expression is fundamentally interconnected, acting as a powerful form of non-verbal communication that allows individuals to convey their identity, mood, and values without saying a word.

One of our customers is a furniture designer who wants outfits that’s in line with his design concept. Another customer who is mid-ages but wants to showcase his young energy in dating.  We also have a customer who said they want outfits that say, “When people are far-away, you won’t notice me; but when people walk by me, they will turn their heads around and think I am stylish.”

Personal style goes beyond the surface level of clothing; it’s a curated representation of one’s self, influenced by their experiences, aspirations, and the world around them. In this day and age, sustainability plays a crucial role in how many individuals perceive their identities, so’s mission to provide sustainable fashion allows them to further express their personal identities.”

Fostering Diversity and Inclusion

The Worlds Times: How would you contribute to creating a positive and inclusive environment for both customers and team members at

Anya Cheng replied, “For our customers, our aim is to provide them with the support they need to tackle their day with confidence. We have a track record of assisting individuals in achieving their aspirations, particularly in environments where they may be underrepresented. From prominent events like Disney Premier, Oscars, Grammys, MLS games, and Cannes red carpet, to guiding career paths in fields such as data science, interior design, and law, we are committed to helping our customers realize their dreams.

As for our team members, we prioritize placing them in roles where they can truly excel. Taelor was founded by two minority women, and we are proud that 67% of our employees are women, with 8% identifying as non-binary. Furthermore, 75% of our workforce represents diverse backgrounds, including Asian, African American, and Latin American individuals. We actively seek out vendors founded by minorities and ensure our models reflect a range of ages, ethnicities, and body types.

In addition, we cater to a wide range of customer sizes, offering sizes from S to 2XL, and provide a waitlist option for those outside of our current size range. Our commitment to inclusivity extends to every aspect of our operations, ensuring that everyone who interacts with feels valued and supported.”

Maintaining Competitive Advantage in a Dynamic Market

Lastly we asked, “Imagine a scenario where a new competitor emerges with a similar mission but different approach. How would you suggest maintain its unique value proposition and competitive edge?”

Personalization at Scale: Our approach involves leveraging advanced data analytics and AI to offer unparalleled levels of personalization in styling services. This ensures that each customer feels uniquely understood and catered to, setting us apart from competitors. It’s important to note that our investment in AI isn’t solely about cost-cutting; rather, it’s about enhancing customer satisfaction while scaling responsibly.

Taelor’s AI serves as the ultimate Outfit of the Day Advisor & Inventory Predictor, offering distinct benefits for both consumers and fashion brands:

For consumers: Our AI technology tailors recommendations to individual needs, enabling users to effortlessly select outfits based on a variety of factors such as occasions, personal style, preferences, and current trends. Moreover, our AI encourages users to explore new styles and step out of their comfort zones, fostering a dynamic and engaging fashion experience.

For fashion brands and beyond: We are at the forefront of Inventory Prediction technology, providing invaluable insights for fashion brands by accurately anticipating customers’ preferences well in advance of pricing factors influencing their decisions. This predictive capability empowers brands to optimize inventory management, minimize wastage, and tailor offerings to meet evolving consumer demands, ultimately driving business growth and enhancing customer satisfaction.

The apparel market is vast, valued at a staggering $400 billion. Circular fashion, including rental and resale, represents a small but rapidly expanding segment within this industry, boasting a remarkable 23% annual growth rate—11 times faster than traditional retailers. This growth underscores the tremendous potential for innovation and expansion in this space.

There exists considerable untapped opportunity, or “white space,” within circular fashion, and we wholeheartedly welcome additional players to join the market. More participants not only stimulate healthy competition but also play a vital role in raising awareness among consumers about the importance of supporting sustainability initiatives.

For instance, consider the stories of women’s rental subscription businesses like Rent the Runway, which launched in 2009, and Nuuly, which debuted in 2019. Nuuly’s remarkable journey to profitability as a unicorn in just four years, with a significant portion of its customer base comprising individuals new to rental services, exemplifies the potential for growth and success within the circular fashion realm.

In essence, the influx of new players into the circular fashion landscape promises to expand the proverbial pie for everyone involved, driving further innovation, sustainability, and consumer engagement within the industry.” Anya Cheng Concluded

Connect with Anya Cheng on LinkedIn

Visit Taelor Style to learn more about it

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