Mike Hollingsworth


Founder & CEO, Hollingsworth Sole


American designer and serial entrepreneur Michael Hollingsworth had grown tired of wearing clothing and accessories made by designers he didn’t know. In 2018, bored with his closet, Hollingsworth decided to pair his proven business acumen with a nostalgia for the bygone era of dressing to impress in Harlem, New York. An epicenter for black creatives, black fashion and black entrepreneurs, Hollingsworth’s soulful Harlem home provided the greatest inspiration for his launch of Hollingsworth Sole.


Coming of age “Uptown” during the 80’s and 90’s, Hollingsworth’s fashion sense was most inspired by the men who raised and mentored him. The pillars of his community were the men who wore suits everyday, opened doors for women, and took pride in matching their belts with their shoes. They taught Hollingsworth the craft of chivalry and the art of hustling. A studious and swift learner, Hollingsworth went on to receive his bachelor’s degree in business management from City College of New York, launch four successful businesses, and author three books. His most successful publication, Mike's Stinking Thinking delivers a powerful, 365-day collection of motivational insights to increase productivity and bring positive thinking into your life. 


A subsequent trip to Italy, fashion capital of the world, provided Hollingsworth with new partners and a golden opportunity to invest in developing 15 different types of sneakers. Initially sold online, during fashion shows, and at special events hosted by popular Harlem Haunt Barrel Wine, these sneakers were the first generation of Hollingsworth Sole products. Today, Michael Hollingsworth oversees branding and production of an unforgettably distinct line of apparel, shoes and accessories for men and women, while proudly building a legacy for his eight children and five grandchildren.