This story starts all the way back in 1865, when Harvard baseball players started sewing big crimson Hs onto the centers of their sweaters. The demarcation meant they were a star player — and, as such ...

Olive, the neutral color you never knew. $395, available at toddsnyder.com Gray wool, leather, and some racing stripes. Can't get much more classic varsity than that. $49, available at gap.com Kind of ...

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Though many men discover fashion after leaving the cosseted Adidas-slide-and-hoodie-safe environs of college, the fresh-scrubbed classic look of the B.M.O.C. (Big Man on Campus)—think rolled khakis, ...