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.
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.
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.
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.
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.
