Preppy Style v. Classic Style

Words by: Chris Hogan

Today 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 preppy style and classic style?

At first I thought, “Well, that’s pretty easy…” Then I tried to talk it out and realized that actually the line is finer than at first glance. While classic style and preppy style both have the same general source – traditional New England “Ivy League” influences – the primary difference can be best described as attitude.

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

They do things like layer an iconic 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 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, most folks just seem to lose their head. Top to bottom “prepped out” looks silly. As with most fashions, trying too hard makes you look 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 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.

When I think of classic style I immediately envision men like Hugh Grant, 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.

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

While the two styles share common roots, there are differences. Understanding those 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.