Hot or Not: The Preppy Guy

Posed smiles and a casual revealing of the polka-dot lining of this dude's jacket.

Costume sketch for Leonardo diCaprio
as Jay Gatsby

You know the one I'm talking about... constantly in a button down, khakis in every color of the rainbow, matching belts and ties. THE preppy guy. Men's fashion changes just as rapidly as women's, but the fashion style that has barely changed over the years is the classic "preppy" look.

Robert Redford as the original
Jay Gatsby

Evolving from casual days in the summer, to frat house cool, to the millions of Vineyard Vines obsessed- the preppy guy has always been there. The preppy guy can pull it off day or night, winter or summer. Since the Prepster-Lite species have sprung up all over America thanks to chain stores such as Vineyard Vines and Sperry, making it easier for styleLESS men to find some style, our definition of preppy has changed. If you wear Sperry's, does that automatically make you preppy? If he opts for salmon shorts instead of athletic shorts, is he equal to Chuck Bass (that's a rhetorical question, obviously no man could ever come close to equalling Chuck Bass)?

He's Chuck Bass

My question to you, dear readers, is this guy cute or juuuuust a little too into fashion to be manly and rugged? Obviously, the preppy look isn't for everyone, but is the preppy guy always hot? Or maybe is he never at all?

Are there extremes of hotness on the preppy scale? The Prepster-Lite, making it possible for teenage boys of America to boost their self esteem through boating shoes all year round, has made its mark on America. Is this lighter version of prep so-called hot? Sperry's instead of loafers, mid-calves over argyle, backwards hats versus driving caps (even though the last time someone wore a driving hat was 1930). Is this "bro" mini-version easier to love, or harder to watch an iconic style slowly spiral down the toilet?

Being preppy, as some say, is a lifestyle more than the act of choosing clothing. Can the way one act and speak be considered preppy? And do these Prepster-Lites fit the description? If you like your guys dedicated Brooks Brothers, Tommy Hilfiger, and Ralph Lauren, click "hot" to the poll on the right. Or maybe preppy pubescent creeps aren't your style, click "not". It's all in the eye of the beholder....even though we can ALL agree that this guy (golfer John Daly, below) should just kick himself in the ass already.

 

        The many looks of Chuck Bass (Ed Westick) and the "Lord" Scott Disick.