Angie, I think it has also to do with the character itself, like the way she is portrait. Anyways, it's funny how that seems to be the 'imaginary' for preppy on Spanish blogs. I never thought of khakis as 'preppy' before! To me, it conveys posh+polished+young adult (kids looking like adults)+college.

Then again, we don't even have a Spanish term for that, so I'm probably wrong in my understanding!

PS: "En cuanto a la mujer, el preppy les sienta como traje de “niña buena”, lo cual puede ser muy clásico y a la vez muy sensual. Es así que para las fanáticas de esta moda va muy bien una falda de tipo colegiala abotonada, con camisa blanca y blazer entallado; en los pies, bailarinas o tacones. Otra opción puede ser una camiseta marinera, con chaqueta, pantalón beige, tipo náutico y zapatos de punta redonda."

Translates into:
"As for women, preppy style looks on them like a little girl's outdit, which makes her look classic and sensual at the same time. A school uniform skirt -tartan- buttoned up with a white shirt and a structured blazer; ballet flats or court heels for the feet. Another option could be a navy/sailor inspired shirt with a jacket, beige trousers and round toe shoes"

@Rachylou, my grandfather, father and brother all attended the same prep school in the South. Charleston and Savannah, in particular are old cities and bastions of Southern prep. The men never stopped wearing their boat shoes without socks all winter, even when it wasn't *cool*, lol! As for the women, sure, some southern women go to town with hairspray (they have humidity you could cut with a knife) but not all of them. Just like any regions, there are a variety of fashion *types*. There is quite a knack to getting your "Muffy in a headband" look without dousing your plaid headband with hairspray......don't ask me how I know this.

To me, "preppy style" means prep school uniforms inspired. What comes to my mind is the show Fresh prince of Bel Air (will smith). Their prep school uniform is what I visualize as prep style. White button down or polo shirts. Khaki pants for men and plaid pleated skirts for girls. Sweaters/vests are either solid, plaid, or argyle. Navy blazers with some kinda of patch for both genders. Sweaters tied around neck. Of course that's the 90s version. I still view today's. Prep style has to be strongly influenced by these elements to be called "preppy".

Blair Waldorf only looked preppy to me when they were in school. After that, she just seemed very feminine to me. I know a lot of these are skewed to the menswear, but this is what I think of as more of a "straight" preppy, without the modern/Californian/rugged twists.

Una nailed the association I mainly have of preppy, which was BIG in my part of the world when I was in middle and high school. Oh, the wide-wale corduroys, the fair isle sweaters, the Docksiders, the hair ribbons, the pants with flamingos and whales and patchwork....aaaaaaah! *runs screaming* I was so very not preppy, can you tell?

I think it has softened now, and I enjoy some elements of it -- popped collars, some of the deck shoe styles like the metallic ones Rae posted recently, etc.

There are definitely menswear and sporty elements in preppy style, to my eye. They seem to evoke a certain kind of athletic, all-American, wholesome vibe. Not body-conscious or overtly sexy in any way.

Thanks for chiming back in, Lemonade. To think that there is even something called Spanish Preppy! I don't know the TV character but I'll take your word for it

Great visuals, Rae. That's how I see Preppy too - which ever Preppy is it.

Just had to chime back in to say that last night at dinner, fiance and I had a great time analyzing all the preppy outfits we saw (we were at a restaurant that seems to be highly frequented by preppy types, even more so than is normal in Boston). We saw a lot of boat shoes, straight but not body-con skirts in madras plaid or khaki, polos on men, and pink shorts on women.

I know this isn't really helpful, but preppy will always be for me the Omega House fraternity from the movie Animal House, and the characters Gregory Marmalard and his girlfriend Mandy Pepperidge.

I do know that here in the southern United States for a man preppy styling, such as myself consists of ensembles such as a Ralp Lauren Polo style shirt and khaki shorts with Sperry boat shoes. For a woman a lot of the time simple sun dresses and sandlea or flats are considered preppy.

Oh wow what a great post. I do think there is a purest type of preppy that is derived from prep school garb. I also agree that there are versions of preppy that are sporty, formal, cocktail...I think the elements of preppy are grounded in American classic. Preppy takes American classic and mixes printed trousers (seersucker, plaids, etc.) with bright jewel tone colors, and a dash of what I consider English country. I also see preppy as the fun side of serious American classics.

I just found this thread and can only describe my college roommate in 1964 fresh from flunking out of a girls' prep school near Princeton. Those days girls did not yet wear pants very often so think white or pastel Oxford cloth shirts usually with Peter Pan collars, small floral print shirtwaist or shift dresses belted or merino or cashmere v neck pullovers over the shirt worn with plaid kilts complete with a giant pin, classic loafers, navy pea coat, navy knee socks, and always a narrow silk hair ribbon tied in a little bow at the top of her head.

Thank you all for the helpful insight on "preppy" fashion. I have added pieces of preppy fashion to my wardrobe without completing the look, I guess. My most common outfits are button ups with blazers, jeans and penny loafers. Or turtle necks with vests, jeans and oxford shoes or riding boots. I like the look of sweaters over button ups but I feel too bulky in them. I also love the preppy look sometimes displaying a "naturally perfect" face (neutrals of makeup), but for me it doesn't work. I love my blush and berry lip gloss too much! Also, what other types of jewelry are preppy besides pearls? I wear my DY cable jewelry. Will that mess up the outfit, if I wanted to go for a head to toes preppy look including accessories? I was not raised preppy and it was not common in my school. We were lower middle class and I was a cheerleader. However, I knew what preppy was and I wanted more. I used to plan visits to spend a day on the boat with my wealthy uncle and I would always be sure to have on my boat shoes, khakis, and a polo shirt. I didn't want him to know, I had very few pieces of his common style. I just wanted to fit in and be one of them. I actually liked when my boat shoes were worn in a bit, so I didn't look like a poser. To this day, as a successful adult, I love the rugby nautical look and I am proud to be able to buy it for myself and my boys (unfortunately my three year old HATES buttons.lol). It might sound silly but I preppy fashion inspired me and still does. Thanks to you all and google, I am reading and learning more helpful tips on a finished look.

It's already been said, but J Crew has definitely changed over the years. It used to be the epitome of prep. And I grew up in the heart of New England prep (one town over from Miss Porter's School, as mentioned earlier, and many others) but as an outside observer (public school for me, by choice).

As J Crew got more fashion-y, especially in the Jenna Lyons era, it's kept some of the preppy touches but they are only a small part of the current J Crew look. Sometimes I still find classic prep things in their catalog: weathered chinos, shorts with small embroidered animals, pale pink oxford cloth shirts, belts made from striped silk ties, boat shoes. Do they still do barn coats?

And the preppy handbook is hilarious! I think there was a reissue recently, updated, but maybe I'm imagining it.

Funny this thread was resurrected. As Queen preppy I must play more. Greyscale we must have grown up near each other!
It's ironic how preppy I am now since I rebelled against it in my youth. I recently found this pin I used to wear (web shot - not my actual hand here). Maybe I'm making up for lost time.

Preppy is always classic but classic is not always preppy. J crew used to be preppy, now not so much. J McLaughlin would be modern preppy. Ralph Lauren is quintessentially preppy. Brooks brothers is preppy. Vineyard vines is sort of preppy wannabe. I don't think Clueless is preppy at all. It is easier to define prep for men, because even the most preppy woman would be influenced a little by fashion, whereas men are generally not. I know people see Betty Draper as a 50's fashion icon, but I see her as preppy. I am of Joy's era and her description of her preppy schoolmate is perfect! I have always dressed preppy and although I like fashion, too, some of my outfits are updated but look like what I wore forty years ago! Tailored pants, a loafer or ballet flat, crisp shirt, and a cable pullover or cardigan, or blazer. I still wear some of the scarves I have collected over the decades.

I just wanted to add to the comment about JCrew changing from their original preppy look. It reminds me of Banana Republic- who remembers the stores and catalogs when their clothes were very safari chic?

I recently came across this definition on Forbes Style File. They were discussing a Ralph Lauren tweed blazer:

The characteristics of a classic preppy look are very simple lines, good quality in fabrics, excellent detailing and elegant colors. Especially in the cooler months this style shows a lot of navy, camel, gray and sometimes red for a pop of color. Preppy style is by nature a bit sporty, but its key elements can add an effortless chic to your office wear when done right.