Single Guys Used to Have Dating Sites and Human Stylists. Now They Have Matchmakers and AI Stylists.

Taelor, an AI-powered menswear rental subscriptions, teams up with matchmaking company Selective Search to offer dressing guidance for single men.

April 4, 2024 — In an era where free dating apps can feel impersonal and overwhelming, many individuals are turning to matchmakers for tailored, white-glove matchmaking services. Simultaneously, the conventional approach of hiring professional stylists and investing in expensive wardrobes from department stores is evolving. Taelor, an Ai-powered menswear rental subscription service, is thrilled to announce its collaboration with Selective Search, the nation’s leading matchmaking firm. Together, they aim to empower individuals to present their best selves confidently in the modern dating scene.

As Taelor recently partnered with the leading dating site Coffee Meets Bagel, this collaboration with Selective Search reflects a growing trend in matchmaking companies and dating sites focusing on enhancing members' appearance and confidence. Echoing successful collaborations seen between dating platforms and clothing rental services like Rent The Runway, Taelor—recognized as the Best Men’s Subscription Box in the U.S.—and Selective Search are joining forces to assist daters in preparing for their dates.

"You might assume that modern technologies like free dating sites facilitate easier connections to find love. However, what we've discovered is that the large number of candidates and lack of curation on these platforms can actually make it more challenging for individuals to establish meaningful connections. That's why our founder, Barbie Adler, a former executive search professional, employs Fortune 500 executive recruitment techniques for personalized matchmaking," explains Julie Verhulst, Vice President of Marketing at Selective Search.

Moreover, after individuals embark on dating, they often realize the need for styling support. Research from Banana Republic revealed that 67% of individuals feel anxious about their date outfits, while studies in Social Psychological and Personality Science have shown that well-dressed individuals receive 27% more likes and messages on online platforms. This highlights the increasing complexity of selecting attire. In the past, matchmaking companies hired personal stylists. These stylists would then source items from department stores for their clients, and white-collar gentlemen paid thousands for dressing guidance and clothes.

Now, with the support of artificial intelligence and the rental share economy model, daters can access highly powerful styling services and wear outfits from over 300 brands and thousands of styles starting at $79 dollars per month. Upon signing up for Taelor’s menswear rental subscription service, Taelor’s professional stylists, assisted by artificial intelligence, curate the perfect outfit to help the customer stand out. The clothing items arrive clean and ready to wear, allowing customers to wear them for weeks. They can then purchase what they love and return the rest of the items when dirty, receiving the next shipment hassle-free. "Besides work outfits, one of the most common occasions that customers inquire about is outfits for date night, and that’s why we are excited to partner with Selective Search," said Anya Cheng, CEO of Taelor.

single guys dating outfit

"Selective Search couldn't be more thrilled about our partnership with Taelor. Confidence plays a crucial role in the dating journey, and by teaming up with Taelor, the experts in men's styling, we're empowering our clients to feel their best selves. This collaboration underscores our commitment to providing comprehensive support to our clients, ensuring they radiate confidence inside and out, ultimately enhancing their chances of finding meaningful connections," said Verhulst.

Traditionally, fashion hubs like New York and Los Angeles have dominated, overshadowing regions such as the Midwest and Silicon Valley in terms of style influence. However, Selective Search and Taelor are determined to rewrite this narrative. Taelor is a Silicon Valley-based tech-driven fashion service company founded by Phoebe Tan, a University of Chicago alumni, and Anya Cheng, a member of Northwestern University faculty and a founding figure of Meta's shopping department. Backed by notable investors like Steve Chen, co-founder of YouTube, Taelor brings innovation to the world of fashion. Selective Search, on the other hand, is the nation’s leading matchmaking firm based in Chicago. Together, they are working to redefine contemporary dating, enabling men to navigate the modern dating landscape efficiently.

Starting this April, Selective Search members will gain access to Taelor’s exclusive deal. In addition to the standard menswear rental subscription plan, which includes a 15-minute consultation or feedback call with their personal stylist, this partnership introduces a special live styling program for daters. “Customers can schedule a 30-minute kick-off call to share their style preferences and wardrobe. Following receipt of their Taelor shipment, they will have a live 1:1 personal styling session over a Zoom call with their personal stylist to learn how to mix and match the items with their own clothes and determine what to wear for each date. Those uncertain about which program suits them can sign up for a 20-minute $20 call to ask styling questions, with the fee applicable towards their subscription service,” explained Phoebe Tan, co-founder of Taelor.

styling consultation

To celebrate, the public can join Selective Search’s matching candidate portal for free at Plus, Taelor offers a $25 discount on clothing rentals with the code “winlove”. Redeem at


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About Taelor

Taelor, an award-winning menswear clothing rental subscription service, is on a mission to help individuals reach their goals in a sustainable manner. Taelor simplifies daily life by providing a professional styling service, ensuring our clients look and feel their best effortlessly. Moreover, our rental model promotes sustainability by significantly extending the lifespan of garments, making a positive impact on the environment. Taelor was recognized by Business Journal as one of the Top 15 Startups to Watch in the Bay Area.  


About Selective Search

Barbie Adler is the Founder and President of Selective Search, a leading national luxury matchmaking firm with the highest success rate (87%) in the industry, resulting in over 4000 happy marriages. A former executive search professional, Barbie's matchmaking service uses Fortune 500 executive recruitment techniques for personal matchmaking, guiding individuals toward lasting love. She has written and spoken extensively on a broad array of topics relating to dating, relationships, and marriage.