1423: Taelor.style: AI-Powered Menswear Rental & Sustainable Apparel Innovation with Fashion AI Tech Entrepreneur Anya Cheng

Tuesday, September 23, 2025

Most men don’t enjoy shopping. They don’t know their size. They procrastinate on buying new clothes until a job interview, first date, or important event forces them to scramble. Sound familiar? What if AI could take that frustration away — not just by telling you what to wear, but by sending you the right clothes, letting you wear them, and taking them back when you’re done? No shopping. No laundry. No wasted time.

https://youtu.be/YDOxeBep_Xc

Anya Cheng is solving this exact problem with Taelor.style. She’s a former senior leader at Meta, eBay, McDonald’s, and Target, and she’s launched Facebook and Instagram Shopping. Now she’s using her experience and passion for innovation to revolutionize men’s fashion with AI, data, and a sustainable rental model. Anya shares how her company helps men “stream” their clothes like Netflix, why goals matter more than fashion sense, and how sustainability and convenience go hand-in-hand. Whether you’re a busy professional, an entrepreneur, or someone looking to stand out or fit in at the right moment, this episode will open your eyes to what’s possible when AI meets fashion.

Quotes:

“Our customers aren’t buying clothes. They’re buying convenience, confidence, and the chance to succeed.”

“Most fashion companies ask, ‘What’s your style?’ We ask, ‘What’s your goal?’”

“Fashion is the second most polluting industry in the world. We’re here to make it circular.”

“If you want a seat at the executive table, forget that you’re a marketer. Be a problem solver.”

“Even with 15 years in big tech, the hardest part of launching a startup was believing in myself.”