The Case of Classic v. Preppy

I want to broach an interesting subject – at least interesting to me. Some while back I ran across the following question: what is the difference between classic style and preppy style?

At first I thought, “Well, that’s pretty easy…” However, when I tried to actually talk it out, I realized that actually the line is finer than at first glance.

While both classic and preppy styles both have the same general source – traditional New England “Ivy League” influences – their primary difference can be best described as attitude.

Where classic style is polished, neat, even orderly, preppy style is a sort of coastline casual. The preppy ethos, best inscribed in the 1980 classic “The Official Preppy Handbook,” is refined irreverence. Preppies essentially seek to bring down the formality of their real or imagined prep school sartorial codes while at the same time keeping them intact.



They do things like layer a blue blazer – the very symbol of proper decorum – under the proletariat functionality of a foul weather slicker. Why? Because they like to sail of course; and if you’re one of them you’ll understand the sartorial irony. Then you’ll also discover you have the same alma mater and go have a G&T at the club.

That, in its essence is the core of the preppy persona: democratized privilege. Let others know you are special, a little blue blooded; but don’t be tacky about it.

On a personal note, this is where I think so many people go wrong with the style today. With the abundance of corduroy, tartans, tweed and waxed canvas, a lot of people seem to lose their head. Top to bottom “prepped out” looks silly. As with most fashions, trying too hard makes you look very sad, not cool.

Well, if that’s my version of preppy than you might think my idea of classic style is less about Martha’s Vineyard and more like lounging Harry’s Bar (the one in Venice, not the one in Paris). Not quite, let’s try Gramercy Tavern; classy and polished but not too snooty.

I make the distinction because when we talk about dressing classically, it is easy to drift into a discussion on formality. While the two are compatible to me they are still mutually exclusive: a bespoke suit is certainly classic, but you needn’t wear a bespoke suit to dress classically.

Classic style also does not hold itself to a particular psychological place like preppy’s clubby-old-school-cum-windswept-sports world. Classic style is more of an approach to dressing. That said, I do agree with a friend’s recent observation that real classic dressing goes back to the idea of English propriety, the precursor to American preppy. So, classic dressing is, in a sense, a more pure form of sartorial expression.

OK, that was a little heavy – I need a drink.

Anyway, when I think of classic style I immediately envision men like George Clooney and the all-time Mr. Classic, Gary Cooper (apologies to J. Hackett). These gentlemen are great examples of defining a sense of individuality within the context of classic dress. None of them look like drones or waiters; there is no sense of stiffness or over-formality. Their styles are elegant but relaxed, well-structured but at the same time seem very comfortable, although without the sand-between-your-toes look of American preppy.

Some men, like Hugh Grant seem to straddle the line between classic style and preppy style. By no means affected, Grant can carry of both looks quite naturally and is a great individual to emulate if you are going for that man-about-town/off-to-the-club look.

Clean lines and traditional bones define the classic outfit. Other keystones include excellent fit, complementary color palettes – often earth tones these days – trim rather than loose silhouettes, and a certain degree of simplicity. No ties with sailboats scattered all over; a charcoal turtleneck rather than a lumpy fisherman’s sweater.

So, while the two styles share common roots, there are some of the differences to look for. Understanding these differences will give you a better handle on getting dressed in the morning.

Classic looks will make you feel urbane and polished; ready for a martini at the bar or a drive to the country in your vintage Bugatti. Preppy will have you out in the bay in a 48 foot Hinckley, hauling in the lines and admiring the new tear in your khakis – just what you wanted.