"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links." If there's something I stand by, it's that I've always been a preppy fashion lover, through and through.

If I were to describe my high school aesthetic in a nutshell, certain pieces of clothing come to mind: popped candy-color Ralph Lauren polos, little plaid skirts, Tommy Hilfiger–branded tennis dresses ...

A Ralph Lauren polo shirt. A varsity jacket. Khakis and loafers. Are these clothes business casual? Date night attire? Is this a “preppy” look? As it happens, the answer is kind of all of the above, ...