The over the top style known as “go-to-hell” in the preppy world is characterized by a blend of sensible and shocking clothing – a blue blazer and white oxford cloth button down paired with Nantucket Reds or a pair of lime green pants embroidered with little yellow tennis racquets, or perhaps a nautical motif. The look might venture into a patchwork plaid madras jacket paired with khaki pants, a neutral colored shirt and penny loafers without socks.
As a style that emerged at country clubs and areas where preppies summer, go- to-hell clothes are a form of fun loving one-up-manship, a way of stating two messages at the same time. The sensible clothing says, “I know perfectly well how to dress with good taste,” while the outrageous item says, “I can be more bold than the next guy and if you don’t like it, you can ‘go to hell.'” But the style still has certain parameters. Not all of the items should be loud and over the top, or the ensemble will look clownish. I refer you to the horrible combinations @ 1:12 and 3:13 in the video above to support my claim.
There is subtlety in nonchalance, a point which the preppy redux in men’s fashion often fails to take into account. Certain designers have gone too far in the go-to-hell direction. They would do well to consider the wisdom of Tom Townsend’s line to Audrey Rouget at the end of the film Metropolitan: “You look really great, and that’s what’s important. You don’t want to overdo it.” For example, I wouldn’t wear a motif belt with motif pants, nor would I wear a brightly colored shirt with brightly colored pants. I would not wear a wild tie with a madras plaid jacket. The more moderate elements of the wardrobe hold the chaos of color in check, which is part of the code for this style.
Not surprisingly, whenever comedians or Hollywood filmmakers want to make fun of preppies, they train their sights on the go-to-hell style. It is an easy mark. Nothing sets off class resentment and laughter more quickly than a “fancy pants rich kid” getting his comeuppance. The assumption is that preppies are stereotypically mean and arrogant people, which I don’t think is true at all. But that’s the whole point of the Alden the Pompous Preppy sketch on Letterman.
Just know that if you wear go-to-hell clothes, you will be asserting the most confident and carefree preppy style there is, but you will also be opening yourself to ridicule from certain people. You have to really own the fun , slightly self-deprecating attitude behind the clothes and display indifference to criticism in order to pull it off. You can’t be preppy if you don’t feel preppy.