Well Heeled

The Prep does not wear trendy footwear, and she never wears shoes that cause her to hobble or walk awkwardly. The Preppy girl owns:


Driving Mocs

These are a wardrobe staple for all preps over sixteen. Available in a variety of colors from Tod’s to Target, the Prep favors Cole Haan, Ferragamo, Gucci, and, of course the classic Tod's. Good driving loafers should be made from buttery soft leather and should have rubber treads for gripping the gas pedal as the Prep zips down the Jaguar E80 in our Aston Martin roadster.  You would never drive that in the States unless you're on your way to a classic car convention, of course; it would be horribly flashy there.

From Salvatore Ferragamo

New Balance 990/991/992/993

The Prep has owned (different versions of) the same exact sneaker for as long as she can remember.  Her husband wears the same ones, just larger.  She owns no other sneakers, except for tennis.  This time-tested line of sneakers is still made in the USA. Worn for exercise and recreation; can also be worn casually (ie. running to grocer). Only the grey ones are Preppy.

Rainbow Sandals
At colleges (NYU, Weslley, Harvard, U of Conn, Northwestern, Yale, Stamford, Georgetown, etc...) we wore almost year round, even if we were in the Northeast. They will be close to our hearts always, and it is our (not-so) secret goal in life to be able to wear them every day once again.

Rogers Navajo
Preferably in gold, though all colors are nice, these are worn in the warmer months for anything from casual to cocktail. Also perfect for wintering in St. Barts.

 

From Jack Rogers

Medium-heeled Sandal
Too high is trashy. These are formal occasions, in gold, silver or black. The Prep only wears these when she has to, and takes the first opportunity to change into her flip flops. The Prep practiced for ages wearing her first pair of kitten heels, but still stumbled just a tad bit at her deb ball. Luckily Mother was too tipsy on G&Ts to notice.  The Prep never talks about her debutante days; it is considered a bit tacky.

Medium-heeled Boot
These are only worn when in the city. Heels in the suburbs or the county are simply wrong. They should be brown or black leather, with a rounded toe and a heel of medium thickness that is about two inches high. The Prep are not completely comfortable in them; she secretly think that they make her look a little bit trashy.

Foul Weather Boot
Hunter wellies (purchased years ago in England, of course) or L.L. Bean's classic Bean Boot (which the Prep calls duck boots) are the go-to choices for inclement weather.


Optional, depending on lifestyle:

Tennis Sneaker
This can hardly be considered optional, since all Preps play tennis. Preps know that running shoes are not acceptable at the club, and white, flat-bottomed tennis shoes are a necessity. There should be a bit of residue from the clay courts in the treads, otherwise people might think that you belonged to a club with hard courts or… the horrors… played on a public court. Grass courts are also acceptable, we suppose; if it’s good enough for Wimbledon, we’ll manage. The same tennis shoes can be used for squash, racquetball and platform tennis.

Sperry Topsider
Daddy spent ¾ mill. on the new boat (not that a Prep would ever mention price to anyone outside the family) and he wouldn’t be happy if the deck got marked because someone wore improper footwear. Because Preps spend so much time out on boats, boat shoes are also worn casually about town. Summer leisure towns that is.... don't go walking around the streets of San Fransisco or New York wearing these everyday. And please don't wear them during winter, these are the quintessential summer shoes so they're to be worn in summer and preferably while in some sort of water craft.

From Sperry

Ballet Flat
The Prep feels that she is going out on a limb a bit when she wears a ballet flat. Because she considers them very French, they constitute her “exotic” look. Worn with skirts, pants and dresses.

Pump
For Preps who work for a living. It really doesn’t matter what it looks like, since  she won’t be working for long. Just as soon as that snafu with her trust gets sorted, it’s back to her rightful place organizing benefits to aid those poor sots who actually need to work.

Dansko Professional Clog
Worn casually by some Preps. These should only be worn if you’ve already snagged a husband whose family is listed in the Social Register (not that the Prep would ever talk about that).

Snow Boot
To be worn only in Aspen at Christmastime or Gstaad in January.

Hiking Boot
Preps go through a phase in college where they decide they love to hike; usually spawned by a prep school paramour who, unfortunately, went to Middlebury and turned a little too crunchy. Break out the boots again when trying to snag aforementioned Social Register’d husband. Your love of the outdoors will impress him greatly.

The Revival of Preppiness- A Double Edged Sword

It's good to see 20 somethings and high schooler's bringing about a preppy revival but there seems a need for some preppy pointers.

Home Decor and Other Interior Matters

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Classifying Prep: what is preppy? Where did it come from? Where is it going?

Where do preppy stylings come from? Some wonder about the about the origins of a style but preppy style seems to be born out of both practicality and privilege. In America much of the preppy basics we see arose from "Old Money."

The old money style comes from Quakers, Shaker, and Pilgrim ideals (some descendents are still alive today) while the newly minted takes a cue from the pomp and circumstantial style of the very top.... who wear it only occasionally but let's not get ahead of ourselves.

Let's take a closer look at the various origins of preppy and study the various groups who gravitate towards prep styling. There are many types of prep groups subgroups today but in my view there are 4 "tribes" (being anthropolgical about it) or categories of you'll see in the western world:

English Aristocracy and the Royals

The quintessential origins that launched preppy style and comes from the top of society (British society that is): Barbour, Dunhill and the like- very expensive quality clothing that lasts and is sometimes bought new but mostly passed down and kept in decent condition throughout the years. Much of it is worn for occasions and practicality; style is an added benefit to wearing it. Today's equivalent is fox/ duck/ quail hunting, horses, country manors, old Land Rovers and mucking about in Wellies on the grounds.

Modern day Duke's, Lord's and Ladies who can tell you about the intricacies of generations of their family history and such. England is where the origins of stereotypical preppy style began generations ago. Maybe further than that. You don't need to call them preppy it's just how they are- they don't really know any other way of dressing.


Old Money/ WASPs'- Across the pond is the American equivalent of English aristocracy, you don't know who their ancestors are (except maybe the Quakers and pilgrims if you trace them way back) or who they are until you know or they realize who you aren('t).

They dress timelessly and traditionally American but try to blend in with everyone else (somewhat, though you can tell they come from money since their body language gives them away and they are cautiously friendly yet guarded with most people who aren't in "their" circle.

They are to be emulated if not for their style, which can sometimes be frumpy (don't let that fool you- their clothes are of excellent quality even though their pant cuffs are frayed at the edges they're nearly 20 years old pants Land End, or J Press who doesn't even make that specific style anymore, in fact J Press isn't even around anymore unfortunately. These are clothes bought before everything was made in China.

Hard to fool old money types them unless you were born in a WASP community or your grandfather was an influential part of history, business or politics 100 or so years ago in some way or fashion. This newly monied grandfather (well, new money at the time he made his fortune that is) set the tone for how the rest of the generations would dress.

Many times they seem like upper middle class suburbanites until they retreat to their old money institutions: prestigious private clubs which at least one member of the family occasionally goes to and various black tie events for various charitable causes. Old money and or WASPY teenagers are often referred to as "trust fundies", they tend to gravitate towards other old money individuals or at least those who have class and know the unwritten rules of old money (dressing loudly and flashily instantly breaks many of these rules) Not always republican so keep the assumptions about political leanings in check (ex: the Kennedy's) If you can tell they live somewhat in the past.

New Money- Recently monied and wanting to show it off. Ralph Lauren shoppers who go to their Lambo's or other trendy vehicle(s) of the year... They tend to mix preppy clothes with other styles thus creating “Noveau prep. A bit gouche in this author's opinion but that's a matter of personal taste...Unlike the more subdued, reserved old money new money are very sociable sometimes to the point of being obnoxious. You have to see the new bright green Seesuckers pants they got to show they're part of the monied set too. As you can tell old and new money don't really get along and sometimes act like oil and water when they're together at social functions. But new money incorporates their background into preppy wardrobe whether it's a Chinese billionaire or someone who just got an investor for their restaurant finding app since it's the goal is to stand out as an individual.

Upper Middle Class Urbanites and Suburbanites- JCrew, Banana, The Gap, Sperry Topsider and North Face (or Patagonia) fleece are the brands of choice for this set for the Prep one's. All bought new, much of it not made the way it used to be unfortunately. Their style came mostly from the 1940's post war boom that embodies the stereotypical "preppy" look.

Influenced by Old Money, Madison Avenue does a great job of marketing the "lifestyle" to upper middle class strivers. It is the style Brooks Brothers and Ralph Lauren sells to upper middle managers and executives in their catalogs and websites. Banana Republic recently did a good job of incorporating the success of Mad Men into it's clothing line which did well with this segment. People want to hark back to the past with a trendy Fidora or skinny tie to stay "current" Though, this sometimes means taking too many trendy cues from the past and coming off trying a bit too hard such as the 1960's preppy trends that are now everywhere and may or may not be a timeless look a decade from now; mostly because certain stores clothing line is based on TV shows and movies.

Upper middle classer's follow trends and sometimes forget Prep styles is a timeless, classic look. A delicate balance and if pulled off correctly may land you in the company of WASPY company who are not sure if they should invite you to their Fisher Island vacation home to meet their other friends.

But most of all the thing that is important is to dress in whichever way that makes you feel good whether it's inspired by Toffs and English Lords or Mad Men- old money, new money or no money. ;)