In the fantasy draft of casual fall outerwear, the best varsity jackets for men are a perennial top pick. From their humble origins as Harvard University baseball sweaters in the 1860s ...

but it also has become a fan-favorite with some of the most iconic celebrities and cool guys ever—Frank Ocean, David Letterman, and Drake, just to name a few. Their jackets are minimalist ...

Shaquille O'Neal purchased letterman jackets for the entire West Port High School football team. The act of generosity stems from O'Neal's relationship with his former basketball coach ...