I’m hope you didn’t intend that to sound as mean and judgmental as it does.
@Joblue The second point is the reasoning for the first. Let’s look to Lilly Pulitzer.
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I own a Vineyard Vines sweater and love it because it looks very good on me. There are no logos on it. It was a gift from my husband, who has no clue about clothing, but saw it and liked the color. I am 53 years old.
Really, people, you can’t assume a certain brand means “preppy” or that the person who wears it is superficial.
@Massmomm The OP asked about why there’s a negative connotation with being preppy. I’m just sharing my opinion. Not trying to offend. I don’t think calling Lilly Pulitzer preppy is an assumption lol.
Thanks everyone. From reading all these posts it makes me realize that the ideal campus is one that has all kinds of kids. I still don’t have a real sense of what the preppy personality is. It seems like preppy describes a syle and attitude perhaps. Anyway, thanks again.
I want to add a note to ‘preppy.’ Genuinely preppy kids who those who are connected to the white, upper class establishment. They are usually socially adept and at ease with people who are already in the power structure - because those people are family and friends of family. They know how to look/act/dress in a way that gives them the appearance of ‘fit’ as future candidates for similar positions of establishment power and prestige.
This was an actual social sub-set culturally in the 50s and 60s in the US, when there was a white power elite that sent their kids to prep schools and then Ivys or elite NE liberal arts colleges or certain southern schools (as legacies usually) and then on to Wall Street, into corporate America, into politics and other similar bastions of power. That era is passing if it’s not already gone. Now ‘prep’ has been turned into a ‘brand’ that anyone can aspire to by purchasing the right clothing and assuming the right attitudes and styles. You can be born poor and black and still be preppy if you choose.
There’s nothing wrong with being genuine prep - it’s what you’re born to - or adopting the prep sub-group if that’s what you admire and aspire to. Or just playing with prep because it’s fun and testing styles for fit is what being in your teens and 20s is about. And schools today that are preppy are schools that either used to attract lots of kids such as I’ve just described - or try to cultivate the aura of a student body born to power and money, or at least aspiring to it.
While several of the posters in this thread have focused on the aesthetic interpretation of preppy, I’d like to say that the original meaning of “preppy,” short for preparatory, has shifted quite a bit. Right now, being a “preppy” kid is more of a statement on your style of dress. However, for students whose parents send them to “preparatory school,” the intent is for them to get into top colleges and be around other students whose parents have similar goals for them.
Why is the connotation negative? It’s because it’s typically associated with wealth, classism and helicopter parents.
I think preppy these days is a pseudonym for Greek. And, OP, from how you described your D it sounds like she could be one of those chameleons who could live happily in that lifestyle. Or not.
And, as for this:
I think it depends on who’s calling who ‘preppy’. If it’s coming from a GDI, then it absolutely DOES mean they are superficial. If it’s coming from a prep, then it absolutely DOES NOT mean one is superficial. You won’t find common ground.
^ it’s been a long time since I’ve heard the term “GDI” 
Never heard GDI. Had to look it up. G-D Independent, yes? As in, I’m not in a a frat (say DKE) but rather GDI?
Well, way back when, GDIs were a little more anti-Greek. There were other middle-of-the-road independents who couldn’t care less either way, so it’s not an either-or thing.
@2muchquan My daughter isn’t a chameleon. If she was I wouldn’t have asked about best fit. She doesn’t change who she is to fit in with others. When it comes to colleges I was confused about type of school she would like, because she doesn’t fall into any one category/stereotype
I think the chameleon was meant more along the lines of someone who is flexible and can feel they connect with a variety of people. I don’t think bit was meant to imply she purposefully changes herself to fit in. More that she naturally does because she has things in common with a breadth of people.
Some people are less flexible and have trouble connecting with others who are very different from them.
Correct, @mom2twogirls.
Not to derail the thread but yes @CaliCash I am familiar with Robin Givhan who writes for my local paper and while I enjoy her articles, she has a very particular point of view and is certainly not the ultimate authority on good fashion.
If LP was good enough for Jackie K, who are we to disparage it 
http://www.elle.com/fashion/g8322/lilly-pulitzer-flower-power/?slide=4
My daughter considers “preps” to be a style of dress (Vineyard Vines, Chubbies, Sperry’s, etc), sports played (lax, field hockey), upperclass wealth and an attitude of privilege/entitlement that comes largely from the kids that attended a private school prior to public HS. They also tend to be big into partying…according to my daughter. Perhaps it is like the poster above that referenced “Greeks”… they are basically kids in training for collegiate Greek life.
Maybe things have changed but the real preppies that I have known, especially in the east, followed zero fashion trends, because the clothes stayed the same year after year. Hence Big brother or sister’s hand me downs even in rich families.
@citymama9 I think your idea of preppy is right on the money. Preppy is, for starters, neat and clean, so no tats or piercings or weird hair or anything like that. Preppy people tend to dress nicely, as in one notch above average. And the styles haven’t changed too terribly much over the past 30 or 40 years: khakis, loafers, button-downs, ect. Just basic, conservative clothing.
I think the conservative dress of preppy people may reflect a certain political conservatism, although it is by no means universal, and that may be the reason some people dislike colleges that are overly “preppy.”
I think OP you could pick a couple colleges – they don’t even have to be serious contenders at this point – and just go visit and see what your D says about the vibe. From there it will gets easier to know what to look for.
I do this with big/small schools for our kids. Theoretically we wanted a small-ish, intimate setting for S #1 – they seemed to suit his personality…but after spending time on campuses he found LACs too “small.” S #2 is acknowledged by his siblings as the family hipster. Yet, he did not like schools that come off as “pretentious”! D is definitely neither preppy nor fashionista but she ended up at a school which is rather preppy and fashionista…because she likes to be the kid that stands out. She is comfortable there and crosses very, very distinct social circles surprisingly well.
Fit is important, It is also important for kids to be prepared to live with other kids who are not like them. They seem to have an instinct for what works, tho, so I would follow your student’s instincts and visit places that can help define a general environment where the students feels he/she will thrive.
Great thread! Chiming in just to add that I think “preppy” (kind of like “middle-class”) is in the eye of the beholder.
When I arrived at Penn in 1978, it was Preppy Mecca. This was in the late 70s, when “preppy style” was hot in contemporary fashion, so I’d already been donning Docksides and (inexpensive) wool crewneck sweaters at my blue-collar, public high school. At Penn (where the vast majority of my friends had attended private schools), I discovered that my clothing choices were wrong, wrong, WRONG, because they were IMITATIONS of The Real Thing, e.g., Sperry Topsiders© (which kids now call “Sperries,” apparently), SKYR turtlnecks, Shetland sweaters from the UK, all cotton oxford shirts (preferably from Brooks Brothers), REAL pearls, etc.
The worst thing one could be was a “poseur” – you weren’t fooling any true prep with that fake stuff! Better just to be a regular shlub.
Of course, not all preps were Old Money or WASP (whose standard issue “preppy attire” was often worn with irony and detachment), and in fact the most conscientiously groomed preppies were often *nouveau riche/i. And certainly they weren’t all conservative. (Lots of northern elites were liberals or Rockefeller Republicans.)
Essentially, the “real” clothing items were class signifiers. A few years later, Lisa Birnbach published The Official Preppy Handbook, and the word “preppy” has never been the same. (She wrote another book 30 years later. Interview here, with some great “preppy history”: http://www.ivy-style.com/preppy-evangelist-the-lisa-birnbach-interview.html.)
Nowadays “preppy” means very different things to different people, but it sounds like your DD, @citymama9, would be happiest at a larger school–if not a university–where there’s a variety of “types.” Most big state flagships and large privates will fit that description (with varying degrees of Greek life), but it will likely require visiting to find the one that feels just right.
My older son attended a genuine old prep (i.e., college preparatory) school, where VERY few students dressed “preppy” because Quakers (in spite of how they’re portrayed on shows like Madame Secretary), don’t wear uniforms (aside from athletic ones), and discourage flagrant displays of wealth. Even though few of the students at my son’s school were practicing Friends, they did have a dress code of sorts (e.g, no camouflage, nothing overtly sexual, no tee shirts with slogans).
Most prep school preppy dressers attended schools where uniforms are required. Tweed or navy jackets, khakis or plaid kilts, oxford shirts, i.e., the classic old “preppy look.”