Michael Hollingsworth

Footwear Designer & Founder, Hollingsworth Sole

Founder & CEO of Hollingsworth Sole, American footwear designer and serial entrepreneur Mr. Michael Hollingsworth aspires to see Black culture well-represented in the luxury brand space. Uninspired and tired of wearing clothing and accessories by designers he didn’t know, Mr. Hollingsworth sought to create a meaningful culture-representative brand experience. Hollingsworth paired his proven business acumen and a nostalgia for the classic era of dressing to impress in Harlem, New York.  The epicenter for entrepreneurial Black creatives, Hollingsworth’s soulful Harlem home provided the greatest inspiration for his launch of Hollingsworth Sole luxury brand experience. 

“Black Americans are the original makers, creators, and curators of American style, here in Harlem we have long cultivated this expertise. We’ve been delivering premium quality to our communities for centuries; I intend to honor this rich legacy”  Mr. Michael Hollingsworth 


Coming of age “Uptown” during the 70's, 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 four 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 exclusive events hosted by popular Harlem Haunt Barawine, 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 six grandchildren.