Many have written to me recently asking if I had a heuristic for differentiating between a Preppy
Outfit and a Preppy
Costume. I had never thought about it formally, but took the opportunity to create a table that may help.
The Difference Between an Outfit and a Costume
| Outfit | Costume |
| Goal: | Functionality, Graciousness, Joy, Wit | Projecting competitive image - "Clothes are a contest to win" |
| Clothes, after put on, are: | Forgotten about | Always front and center |
| Movement is: | Enabled by clothes | Restricted by clothes |
| People leave the wearer: | Inspired | Depressed, uneasy |
| Style worn: | Even if alone | Only in public |
| Clothes: | Reveal the wearer | Mislead or overstate information about the wearer |
| Alignment (between other items worn, work clothes, casual clothes, social outfits, private outfits, even house and car): | High | Low |
| Age: | Old and new | Almost all new |
| Clothes: | Improve the entire scene | Highlight the wearer at the expense of the scene |
| Vendor Example: | 1980 L.L. Bean | 2011 L.L. Bean Signature |
"I've always wanted to pretend to be an architect!" - George Costanza
Some people, when wearing well thought-out clothes, look great. Other people look as if they should be carrying a UNICEF box and a plastic pumpkin for candy. The difference can seem subtle, but the change in feeling one gets is incredibly strong.
Graciousness vs. Ostentatious
There is a big difference between being gracious and being ostentatious. Dressing well should be a form of good manners. (One thing I have loved about all of my Volvo wagons over the years is that they don't have the same "look at me"-ness of other flashier brands, while still giving guests a pleasant ride.)
Private vs. Public
My father often wore one of his J. Press bow ties with an Orvis Battenkill tattersall shirt, even if he didn't venture out of the house. So my question is always, would you wear the same thing if no one was going to see you?
Alignment
The countless people I have known who are "the real deal" have an alignment throughout all aspects of their lives. While everyone's passions and interests vary, there is a thread that carries through from clothes, furniture, houses, cars, and hobbies. When this alignment is not there, the effect is similar to reading a misleading resume or hearing an inaccurate story. It is a lot more work because it doesn't add up.
It used to be that the Preppy wardrobe was an indicator of a lifestyle that included social responsibility. Now so many want the image without the work. So instead of canoeing around Squam Lake or Winnipesaukee counting loon chicks, they are jumping on the jet skies (but wanting to wear the old-guard iconic tartans to project gravitas and credibility).
Improve the scene vs. standout
Does a person want to improve the scene of which he or she is part or do they want to stand out in it? This extends beyond clothes. I've known people who move to a lovely street filled with moderate sized wood shingled houses, which they professed to love, and proceed to petition the zoning board to construct a mammoth contemporary house on a tiny lot. If they are successful, both the new house and the old houses look terrible. These are the same people that maneuver to be in the center of any staged group photograph.
It can be a bit murkier
Of course, there are aspiration clothes. A lot of kids wear costumes as part of their "learning to be" and to try on different images. As with so many things, what is charming and appropriate in the below-25 set becomes awkward and embarrassing as people pass that mark. (Meanwhile, I love my rope bracelets and my pearl earrings yet they are completely non-functional. And I have also always had an affinity for the whale motif. )
The Big Rule
My cardinal rule after being with someone, visiting their house, or even now, visiting their blogs or other sites is to ask 'how does it make me feel when I leave?' Do I feel inspired, relaxed, and intellectually satiated, or do I feel stepped on and manipulated? At times it is difficult to pinpoint exactly why I feel this way, but I have learned to let that feeling drive the analysis.
Here is a summary irony. Just as James Bond wouldn't carry a James Bond lunchbox, so too are Preppy costumes the antithesis of preppy.