I've decided I need more WASP-y stripes like this in my life.
Speaking of WASPs, I had a conversation like this with my neighbor this weekend when we walked to Easter on Parade. I was looking at his Brooks Brothers catalog and while everyone in there was decidedly beautiful, there is such a thing as too preppy. And I like preppy. I went to UR, after all. 2 of my major boyfriends have been preppy. But too much preppy that screams WASP or Daddy's Money, I have a problem with. In researching this article, I was suprirsed to find quite a few preppy-centric blogs and websites. Here are some illustrative examples.
Good Preppy:
Boys with bikes/glasses/ties
This is Matt Bomer (unfortunate name for him) who stars in USA Network's White Collar, which is a good show. This is from a Glamour spread that I have as well. This look is really more hipster-preppy though.
Anything White
Especially Eyelet. So dainty and feminine.
Stripes and Argyle (in moderation)
Especially shirtdresses. I think I saw this blue and white number on a gal at Easter on Parade and I covet.
(Posh Tots)
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Bad Preppy:
Sweaters tied over your shoulders.
You look like a douche if you are guy and like a soccer mom if you are a woman. 
Vera Bradley
I am a proud member of the Facebook group Your Vera Bradley Bag is Not Unique or even Attractive because after I graduated, EVERYONE on campus had this type of handbag. And the FB group just says it all for me.
Madras (see also: Seersucker)
Obviously a madras suit would be overkill but I don't really like it in general because everyone wears it. I don't like it when everyone dresses the same in general. (ala, Strawberry Hill Races, or Pig Roast at UR, or in the oversized seersucker suit I saw my college ex wearing at Easter on Parade this past weekend)
Printed Pants
Alligators, whales, horses, ducks, I don't care. You look ridiculous.
I actually own this book, which I bought as a joke at a used book sale.
(Worthy Style)
I will say, like most styles, if you have the confidence and that certain something to pull these looks off, I will give you a pass.
I love that white eyelet dress Eva is wearing! How gorgeous! I laughed at loud at your don'ts - I so agree with you, especially about those Vera Bradley bags. UGH. I remember when those became popular and it seemed like every other girl in Blacksburg had one. I can't say I was ever a fan. They look too much like quilted diaper bags to me.
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