In the 19th century and the beginning of the 20th century, tennis players wore polo shirts because of the ease and comfort of the shirt itself. Today, the great thing about polo shirts are they can be worn formally or casually. Polos are worn as school uniforms or as a shirt to the office, where t-shirts are not acceptable.
Here, Preston wore his J. Crew polo shirt during a night out in Pasadena, CA with me and our friends. Pairing it with khakis and sporty Pumas, it was a comfortable, semi-formal look.