Tommy Hilfiger – $27.5 Million, Florida

Tommy Hilfiger is a fashion designer and his name is a world famous brand. He started his corporation in 1985, while prior to that, he co-owned a boutique chain, People’s Place in NYC. At first, Tommy focused on menswear but later transitioned to women’s clothing, perfumes, and other luxuries. In 2013, Tommy received the Geoffrey Beene Lifetime Achievement Award and in 2016, he published his memoirs. In 2017, his Florida mansion was listed for $27.5M. It features 14,075 square feet of space, 12 bathrooms, seven rooms, and an oceanfront pool.