Mugsy is a Chicago-based direct-to-consumer menswear brand built around a single idea: men shouldn't have to trade comfort for style. Founded in 2015 by Leo Tropeano, the company designs stretchy, athletic-fit jeans, chinos, shorts and shirts using a custom performance-denim blend that adds more spandex and softer cotton than typical stretch jeans. Sold almost entirely online with free shipping and returns, Mugsy has grown into one of the fastest-growing apparel companies in the U.S., earning more than 40,000 five-star reviews and a spot on the Inc. 5000.
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.