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Menswear-Centric Taelor Shakes Up the Subscription Box Market

The question of how to make fashion more sustainable has persisted over the past few years. More often than not, the materials are the first to be addressed. More recently, however, the supply chain is receiving attention, from where and how clothing gets made to how it’s eventually disposed. 

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Subscription services have entered as a solution to cut down on the amount of textile waste while allowing consumers to explore various garments to find what suits them.

Over the past few years, Taelor has started making a name for itself, first by focusing on menswear and secondly by combining artificial intelligence (AI) with recommendations from stylists.

What is Taelor?

Based out of Silicon Valley, Taelor is a menswear subscription service that incorporates data analytics to find what aligns with a customer’s tastes and secondly to function as a product-testing platform for brands and retailers. 

As the vision of CEO and founder Anya Cheng – a former product lead at Meta who helped helm the Facebook Shopping platform – Taelor kicked off in 2021, launching to a group of pilot customers.

Taelor's Founders
Taelor's Founders, Anya Cheng (left) and Phoebe Tan (right)

Cheng sought to develop a platform that allows access to a broader range of high-quality menswear styles, ideally for someone seeking to look good on and off the job without having to put in significant effort, and provides a more sustainable alternative for style exploration. 

Similar to other style box services, users signing up for Taelor first fill out a style questionnaire before receiving a consultation from a stylist. This information, refined through AI, results in clothing more tailored to the customer’s interests and personal style.

After, the clothing gets shipped to the customer, who can wear the pieces for a period of time – up to multiple weeks – and then opt to return them or make a purchase, which is priced about 70-percent lower than retail. 

Each box includes four items picked across shirts, Henleys, sweaters, and jackets, with garments ranging from traditionally constructed to high-tech and performance-driven and retailing on average for about $200. Taelor expects to soon expand its selection with trousers.

For a flat $88-per-month fee, customers can receive up to two boxes, and both shipping and dry cleaning are free of charge. 

Already, Taelor has received significant recognition, including winning first place at Draper Demo Day, selection for the Taiwan Tech Arena Silicon Valley partnership program, and receiving mentorship from Twitch co-founder Kevin Lee and Rotten Tomatoes co-founder Patrick Lee through the SPARL Accel program.

Expansion Plans

Especially in an increasingly competitive market, a brand needs to not just stand out but go to where the customers are. 

Taelor is in the early stages of expansion, pushing ahead through a streamlined yet nuanced approach to menswear. Going into 2022, $2.3 million secured through a pre-seed round of funding provides the support needed to grow.

Bling Capital – founded by former Google and Facebook executive Ben Ling and an investor in previous unicorns like Everlane, Instacart, and Lyft – has provided the greatest degree of funding so far, followed by investments from Samantha Chien and her husband, Guitar Hero founder Kai Huang; Sunny Huang, operator for Smart Capital and the Executive Director of NewWide Group, a major manufacturer of apparel for LuluLemon, Adidas, and over 200 other brands; Sean Chao, a former managing director at Morgan Stanley Taiwan; angel investment group Chicago Early; and the Silicon Valley Chapter of Golden Seeds, which focuses on female-led companies with significant growth potential. 

With this funding, Taelor eyes multiple partnership opportunities, including offering its subscription as an employment benefit and collaborating with brands to anticipate trends, lessen the volume of unsold products, identify new customers, and uncover more about consumers’ interests. 

Already, Taelor has forged partnerships with over 100 brands spanning mainstream options to independent, sustainably oriented companies.

Considering the growing number of styles out there for men, these range from everyday basics to smart-casual office fare to edgier streetwear and something for date nights and more formal occasions. Brands eyeing sustainability are given priority. 

Taelor Product Yellow

Currently, partnerships encompass Western Rise, known for pairing more timeless construction with versatility and performance; Koup, an activewear brand constructing its garments out of recycled plastic bottles and cinnamon; Sons + Fathers, a small-scale brand started in 2020 by Vishwajeet Singh Rana focusing on ethical construction from material sourcing through manufacturing; [REESEDELUCA], a line of gender-free basics and loungewear using all-natural plant-based fabrics; TRANZEND, a U.K.-founded brand constructing performance garments out of recycled plastic bottles and coffee grounds; and Landway, an outdoor-centric brand making garments from recycled polyester and other fibers with the goal of reducing its water consumption. 

As Taelor looks ahead, we had an opportunity to speak with Cheng and co-founder COO Phoebe Tan. Beyond advancing the intersection between Facebook’s platform and ecommerce, Cheng’s experience additionally includes expanding international business for eBay, mobile and tablet commerce for Target and Sears, teaching product management in a journalism class for Northwestern University, publishing multiple books, and giving TED talks. 

Tan, meanwhile, focuses on Taelor’s operations, supply chain, and financial side. Prior to founding Taelor, she was an operations partner for Amazon Go and Starbucks, as well as overseeing catering for Singapore and Emirates airlines.

Starting up Taelor aligns with Tan’s dream of becoming a designer and current aspirations of a more minimalist, environmentally conscious fashion industry that caters more closely to customers’ tastes. 

Most subscription box services typically start with womenswear before they branch out to menswear. What influenced your decision to start with menswear?

Anya Cheng: I wanted to look good for my job, dates, and social gatherings, but I didn’t have a good fashion sense. I didn’t want to spend time chasing after clothes, so I was wearing the same thing all the time. 

I considered using Stitch Fix, but with Stitch Fix, you have to buy something from every shipment, and I didn’t want to own that much stuff. I started using Rent The Runway five years ago and fell in love with it. I haven’t purchased any clothes since. 

But, I realized that all rental subscription services are for people who are into fashion and are willing to spend LOTS OF time browsing through items. They are not designed for people who simply want to dress up to achieve a goal.

I worked with a former Nordstrom researcher and interviewed more than 500 people. I found out that many of them have the same problem as I do. And you know what? Most of them are men.

That’s why I started Taelor, an AI-powered menswear rental subscription service that helps busy men look good without the commitment of buying clothes.  

Over the past 10 years, outside of my corporate career, I have also been volunteering as a life coach. I have mentored hundreds of people who are all looking to achieve their own personal goals, and I’ve realized that I am not the only one who is looking to become a better version of myself.

Through mentoring, I’ve learned that feeling confident is essential to achieving success. And usually, all people need to feel confident is a little help.

That’s also what inspired the idea of Taelor – to help busy professionals feel more confident by helping them dress stylishly without investing lots of time. . 

It’s just like Queer Eye, the Netflix show that helps people by giving them a makeover, which later helps them achieve their life goals. 

I teamed up with my University of Chicago Booth School of Business classmate Phoebe Tan, who dreamt of being a fashion designer growing up.

She ended up becoming an operational expert who has served clients like Amazon Go, Starbucks and Singapore Airlines. She is passionate about helping the fashion industry to be more sustainable through circular fashion. 

I also involved my old coworkers – a group of Silicon Valley executives – including an artificial intelligence patent-owner who has worked at Google, Facebook, and eBay, fashion stylists from Stitch Fix and Le Tote, and more. 

We named the company Taelor, which phonetically is the occupation “tailor” and is a name for a real person. We believe Taelor is for people just like you and me — normal, everyday people who have a dream. And we’re looking to help you achieve it. 

In the release, you mention an “access, not ownership” approach to menswear that’s designed to be more sustainable. What benefits does Taelor offer for someone looking to explore their style? You primarily describe your targeted customer as someone younger and interested in making more sustainable fashion choices. Who, demographics wise, has been drawn to Taelor so far?

Our customers are mostly 25- to 35-year-old men who are busy but ambitious. They live all over the United States and are engineers, people-facing professionals and sales people. Half of them are not married.  

Taelor Customer

Our customers love us because they don’t need to think about their outfits anymore. Our AI and stylists pick clothes they love.

Also, because there is no pressure to buy, they can try a variety of styles outside of their comfort zone without considering the purchase price or the hassle of laundry. For them, it’s not just about looking good, but with Taelor, they have peace of mind and feel ready every day. 

How will the recent round of funding help Taelor grow? What are your plans going forward for Taelor?

In the next 18 months, we have three key milestones. We plan to open service for wait-listers — now we only offer sizes small and medium, and we’re opening up for more sizes. This means investment in styling and operations. 

Second, we want to test different marketing channels such as corporate gifting and dating site partnerships. We plan to double down on those areas, and we plan to hire salespeople and offshore engineers. 

Lastly, we plan to serve a few thousands of customers, which will get us a significant number of data points for AI and enable us to monetize the data via a B2B SAAS model. That means that we will be able to sell the data to clothing brands and retailers who want more insights on the kind of clothes that people like, so they can better predict trends.

You mention working with corporations to offer style services as an employee perk. How does this model work, and how does having access to this service benefit employees?

Taelor plans to work with corporations to offer its subscription service as a perk or gift for employees and clients.

The way that our corporate deals work is that corporations can use Taelor to send a welcome box to new employees that includes one swag item plus a personalized note and a code for Taelor that is good for three months of the clothing service.

Companies may choose to cover the entire cost of the subscription for their employees or they may simply choose to offer a discount for their employees.

We think offering a clothing rental subscription would be especially helpful for new employees because it will help them build confidence. The first three months after someone is hired are critical for new employees to be successful.

Taelor Model With Product

Employees who perform better are more likely to succeed in their first two years. Confidence increases performance, and looking good helps increase confidence. 

Plus, new hires usually feel overwhelmed and don’t have time to dress up to impress. Sending out swag is ok, but it’s not very sustainable. Most swag ends up in a landfill. By offering a subscription to Taelor for new employees instead, corporations can help their employees feel more confident and help save the environment.

Taelor is the gifting partner of leading corporate gifting, providing Giftpack, which serves Google, Netflix, Facebook and more. Taelor is also an employee benefit perk of Google.

You also describe Taelor as a place for brands to test their products. How has this been working, and what do you use to gauge customer response?

Right now, Taelor has strategic investors in the fashion industry, and we are hoping that those strategic investors will introduce us to many different fashion brands who may be interested in becoming one of our partnered brands to have their clothes carried on our site.

And yes, those brands that we agree to partner with us will have their clothes included in our subscription boxes, along with other brands that we carry.

However, whenever we enter into a partnership with a clothing brand, we always make sure it’s a brand that carries high-quality clothes that make sense for our customers. 

The way that brands are able to test their products is that we request feedback from customers on each box of clothes that they receive. When they send the clothes back, they have to tell us how each piece of clothing fit and whether they liked it or not.

That feedback is then turned into data that can be sent back to the clothing brands to let them know how people like the clothes. It’s a great way for brands to test out products before they start selling them to the general public.

We also provide aggregated trend insights from our customers’ feedback of different brands, so each brand can know what’s trending in general.   

Use the code DAPPER to get 20% off your first two months of Taelor’s menswear rental subscription and the code DAPPERGIFT to get 20% off a one-time gift card purchase at


Ivan Yaskey is a Philly-born menswear fashion blogger and copywriter. When not writing about men's style he's also an EDM and synthpop enthusiast.