7. Calvin Klein and his simple, elevated style

Houston Street sign where New York fashion designer Calvin Klein's billboard sits.
The iconic Calvin Klein billboard is on Houston Street.

Growing up minutes from Ralph Lauren in the Bronx, Calvin Klein found a love for fashion while he visited his grandmother’s tailoring shop. From here, he sketched his imagined designs before achieving any formal fashion education. After studying at the High School of Art and Design, Klein attended the Fashion Institute of Technology. With his experience interning for Dan Millstein, a suits and cloaks manufacturer based in the Garment District, Klein founded his company with childhood friend Barry Schwartz in 1968. By September 1969, the New York fashion designer was on the cover of Vogue.

Today the Calvin Klein brand sells simple, understated clothing. In New York City, Calvin Klein advertisements have occupied a large billboard on Houston Street since 1999. Standing 55 feet by 75 feet, the billboard has started the careers of many models. In recent years, the Calvin Klein brand has strived to feature underrepresented groups of people. In June 2020, model Jari Jones stared fiercely onto Houston Street as one of a handful of Black transgender models to be featured on the billboard.