Taelor is an AI-powered menswear rental subscription that pairs machine-curated outfits with human stylists so busy men can dress well without thinking about it. For a flat monthly fee, members take a short style quiz, receive boxes of real clothes to wear for weeks, return what they don't want in a prepaid bag, and buy favorites at a steep discount. Founded in 2021 by Anya Cheng and Phoebe Tan, the company positions itself as the 'Rent the Runway for men' and runs on a circular, lower-waste model.
Anya Cheng is the Founder & CEO of Taelor, an AI-powered men's clothing rental and styling subscription service that raised $5M+ and ranked #1 in U.S. menswear rentals by GQ. A Taiwanese-American first-generation immigrant who spent 15+ years at Target, McDonald's, eBay, and Meta (where she helped launch Facebook Shopping), she pivoted to entrepreneurship to solve a problem she saw everywhere: busy professional men who needed to look sharp but hated shopping. Taelor combines AI trend forecasting with human stylists to deliver curated wardrobes to subscribers, tackling fashion's 30% waste problem along the way. Cheng also teaches at Northwestern's Medill School and mentors at 500 Startups.