We're talking about classics because men, in general, buy to build not because of fads or what's in fashion.
A classic however preppy is the madras shorts. It's your opportunity to add a dash of dapper color without turning too many heads or raising eyebrows....we love the basic pair found at Orvis or these from Brooks Brothers.
If you don't own them, consider a pair....because if you have a work-related BBQ or a weekend in the Vineyard, this is what all of your counterparts will be sporting!
