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, 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 E80 in our Aston Martin roadster. She would never drive it in the States, 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.
At our expensive liberal arts colleges (which we often equated with summer camp), we wore these year round, even though 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.
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
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.
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:
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.
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.
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.
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).
To be worn only in Aspen at Christmastime or Gstaad in January.
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.
Golfing always reminds you of the course in South Africa on which Daddy first taught you. If only that trip hadn’t gone bad when Daddy gave the au pair those big diamond earrings and Mother got mad and made him send her back to France…