The Preppy Home

The Setting: Location, Location, Location Because it is essential that Preppy offspring meet the “right” people in his/her hometown, the location of the Preppy Home is crucial. The Preppy Home is set in an established neighborhood with lots of mature trees. The Preppy Home may be in the city or the country, or sometimes, the suburbs. Older suburbs are acceptable, but newer, subdivisions-cum-suburbs, are despired by Preps everywhere. Examples of Preppy suburbs are Brookline, Massachusetts; Bedford, New York, McLean, Virginia; Darien, Connecticut.

The Exterior
There are a few different types of Preppy Home. Styles vary based upon region, lifestyle, and, of course, personal tastes. As a rule, Preppy Homes are based upon high quality, natural materials. Old homes are preppy; the older, the better. New construction is NOT preppy.  Bonus points for an architecturally significant home.

Brick, wood and stone exteriors are favorites for the Preppy Home. Vinyl or other synthetic siding is a big no-no. Vinyl is not preppy.

The Interior
Preppy interiors include original hardwood floors (of course), which are usually covered with antique Oriental rugs. Faux Orientals are a faux pas; a prep who is so unlucky as to not have heirloom rugs handed down should leave floors bare or cover them with inexpensive, “I’m-not-trying-too-hard-and-these-just-work-with-our-busy-lifestyle” sisal or hooked wool rugs. Wall-to-wall carpeting is NOT Preppy.
The Prep Home is filled with original artwork and antiques. If it has not been passed down from family members, the Prep goes antiquing, slowly collecting pieces that cannot be found at Crate and Barrel or Pottery Barn. Although she has classic taste (never trendy), the Prep has a sophisticated eye, culled from extensive travel during her formative years. She learned grace and personal style at home, but most of what she learned about art, architecture and antiques, she picked up in New York City, London, Paris and Florence in museums, galleries and private homes. The Prep does not redecorate, she curates.

Preppy Regional Style

New England

The New England Preppy Home is part colonial home, part English manor house and part hunting lodge.  L. L. Bean style abounds. New England color schemes often center on the colors at the epicenter of the Preppy universe: Navy blue, hunter green and maroon.  Although the phrase only originated during WWII, New Englanders have been adhering to the WASP adage: "Use It Up, Wear It Out; Make It Do, Do Without," since they lived across the pond, and it is reflected in both their homes and their personal style. It informs their affinity for antiques (“hand-me-downs”), Grandmother’s furs, Mother’s jewelry and even Father’s old sweaters. To A New England Prep, a threadbare cushion does not signal poverty, but rather serves as a reminder of the generations of [insert family name here] that have relaxed on this armchair before us. Because of her affinity for history, the New England Prep rarely buys new things for her home. Why should she, when she has the club chairs from Grandfather’s old Beacon Hill office, the walnut dining set that Great-Grandfather gave Grandmother as a wedding gift, and the brass andirons that a distant relative carried over on the Mayflower? After all, things just aren’t made like that anymore…

The South
While the New Englander can precisely detail the life of every member of her family back to 1620, the Southern Prep tends to emphasize her family history only back to the genteel decades preceding the War of Northern Aggression. This is because many Southern Preppy families only became “established” in those decades, as they grew rich off of their Peculiar Institution. As such, the Southern Preppy interior is newer and more feminine than its New England counterpart. Like the New England Prep, the Southern Prep is influenced by Colonial décor, but the Victorian era brought muted colors and sumptuous fabrics to the Southern Preppy Home, and the Art Deco period lent clean lines and geometric shapes. Post-WWII interior design is not for Preps.

All true Southern Preps are descended from at least one Confederate General, and his large portrait, in muted oils (done in uniform of course) hangs like a badge of honor in the formal living room. Non-primary colors, floral prints and stripes abound in the Southern Preppy Home. While it might include the time-honored traditional preppy colors, a Southern Preppy Home might also have a formal living room done in pinks and greens, or a dining room with coral walls. While the New England Prep might consider a Southern Preppy Home to be showy or even a bit gaudy, the Southern Prep would likely believe the New Englander’s home to be drab, shabby and possibly outdated.

Preppy Accessories: The Preppy Man

The Preppy Man

Photo from Ralp Lauren

A Preppy Man is the most imoprtant accessory for a Preppy Woman.  Attire for the Preppy Man is even easier than for the Preppy Woman. Preppy men learned to dress in Prep School, and haven’t changed their style since. Think of male Preppy dressing as a uniform, with the only thing that changes being accessories.

Casual
Button down (Ralph Lauren, Vineyard Vines or J. Crew) or polo shirt (Lacoste, Vineyard Vines or Ralph Lauren), tucked in
Khakis- Plain front, light tan khakis (J. Crew’s in Stone)

Footwear- Sperry Topsiders, New Balance 993 Sneakers or flip flops (Rainbow), L. L. Bean boots
Accessories- Ribbon or needlepoint belts, Oakley or Ray Ban sunglasses with Croakies, baseball cap from regatta or alma mater, sweater or Patagonia fleece if chilly

Cocktail/Business
Navy Blazer With Gold Buttons

Photo from Ralph Lauren

White Button Down
Khakis
Footwear
Accessories- Colorful tie (Vineyard Vines, CK Bradley, J. Crew). Variation: Colorful bow tie

Formal
Classic Black Tuxedo
Too many G&Ts

Preppy Beauty: Less is More

CK Bradley, shown here on a magazine cover, epitomizes preppy beauty

Preppy beauty is always natural and minimal. Overly done hair and makeup are considered cheesy by Preps.

Skin
The lynchpin of Preppy beauty is healthy, glowing skin. The Prep knows that eating well (most of the time!), exercising and wearing a moisturizer with SPF makes her not only feel good, but look good, too. The Prep always washes her face before bed (even if she has been drinking Champagne all evening!) and has a standing appointment with her city’s top dermatologist.

Hair
Preppy hair is, for the most part, left the way God and nature intended it. Blunt cuts of chin length, shoulder length and mid-back length are acceptable. Ponytails and headbands are the most common variations from the unadorned, side-parted look. The luckiest Preps (many of them) are born with thick, straight, shiny hair in a blonde or dark brown shade. Preps that are curly, frizzy, or limp in texture usually favor ponytails. Preppy hair should not be colored (before age forty, that is).

Makeup
Makeup is minimal, if worn at all. The goal of Preppy makeup is not to look as though one is wearing makeup, but to look as though one has spent the day doing some invigorating activity in the sun. Flaws can be subtly covered with a bit of concealer, and a touch of blush or bronzer gives the cheeks a healthy glow. A swipe of mascara may be used to accentuate the eyes. Makeup should never be noticeable or “caked on.”

Scent
Generally speaking, perfumes are not Preppy. Many Preps have a favorite scent, usually discovered in France or Italy, but this is best saved for special occasions. If perfume is to be worn, it should be subtle. We repeat, subtle.

Preppy Accessories: Footwear

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 Moc
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.

Rainbow Sandals
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.

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.

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.

Golf Cleats
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…

Preppy Accessories: The Tote

L.L. Bean Boat ‘N’ Tote
The Prep has used this classic L.L. Bean tote - monogrammed, of course - for as long as she can remember. She was certainly exposed to it in utero on her parents’ frequent weekend jaunts to the Hamptons (“before they were popular”). This tote is especially useful for packing the Range Rover to head to Nantucket, carrying a bocce set to Oyster Bay or toting sample favors for a Met benefit around the city. High school and college-aged Preps also use this tote in lieu of a handbag.

Longchamp Pliage
The Prep fell in love with Longchamp on her first trip to Paris, and the affair has not cooled.  Le Pliage is versatile, going from school or work to Martignetti's to the beach with ease, and it comes in many colors, from pastels to brights to neutrals, to complement any Prep wardrobe.

Vera Bradley
The Prep loves Vera Bradley primarily for its luggage - the colorful duffels in pretty prints are perfect for hopping on the Jitney on Friday afternoons in August - but also loves their totes for their durability and ease of care (they’re machine washable).

CK Bradley
The Prep first discovered CK Bradley when the designer held trunk shows at the Prep’s boarding school or college campus, and she immediately fell in love with the bright colors, fun prints and whimsical designs that the label is known for. Many Preps faithfully carried their first CK Bradley tote every day for several years straight in high school or college, despite the stains and frayed edges that would inevitably occur with such prolonged use.

Prep 101: Preppy Dressing for Novices

The preppy wardrobe starts with a few basic pieces and builds from there. Preppy style is not trend-driven and does not change a great deal over time. Preppy clothing changes gently through the decades, with hemlines, pants cuts and hairstyles changing, but the basic idea remaining the same. Preppy style is not age specific. The same Preppy outfit could be found, varying only slightly, on a five-year old, a twenty-year-old or a seventy-year old.
Sweaters
Cable-knit cashmere is the favorite sweater of Preppy girls the world over, and it is sublime with a strand of pearls laying across the crew neck.  When a Prep wants to mix it up (just a bit!), she may wear a Fair Isle knit, a cable-knit in cotton, or a cashmere turtleneck.
Button-down Shirts
Classic button downs are a Preppy staple. Ralph Lauren oxfords in a rainbow of pretty pastels are favored by all ages, while crisp white button-downs are an excellent choice for Preps seeking a casual yet elegant look.

Photo from Ralph Lauren

Polos
Preps were raised on Izod, and the little alligator is an integral part of the Prep psyche. After the Lacoste/Izod split, Preps ceased to wear the (newly mid-range) Izod brand, but remained dedicated to the upmarket Lacoste label.

Khakis
Every Preppy girl has her fit, and she rarely wavers. Her favorites may be from Ralph Lauren, J. Crew or J. McLaughlin, but she knows what fits her and sticks with it. Khakis are in a light tan (never a dark, muddy color) or, occasionally, a pastel or bright.
Skirts
Just-above-the-knee skirts in straight or A-line cuts are a Preppy staple. Corduroy is worn in the Fall, and khaki, seersucker or a Lilly Pulitzer print works in the Spring or Summer. Occasionally, the Prep will take a risk with a denim skirt, but this usually doesn’t work and is not advised (exception: The Preppy Cowgirl look, which is usually worn on Halloween and on trips to Texas or Big Sky Country).
Denim and Corduroy
Denim and corduroy are Preppy essentials, but only in the Fall and Winter months. Corduroy is acceptable from anywhere khakis are purchased, but in the past decade, preppy denim has taken an up-Preppy turn with the proliferation of designer jeans. Seven for All Mankind; Citizens of Humanity; Paper, Denim and Cloth; Joes’s Jeans and other brands make good jeans which can be integrated into the preppy wardrobe. However, a classic boot cut style should be chosen, and a Prep never, ever wears jeans with crystals, beading, Girl-Scout-esque patches or other adornment. While they should be flattering, jeans are purely functional (even if they cost $160.00).
Casual Dresses
Printed shifts (Lilly Pulitzer) are favored in the Summer months, while printed wrap dresses (Diane von Furstenberg) keep Preps warm in the cooler seasons.  New York brand J. McLaughlin is a favorite of Preps for dresses in particular, but everything that they make is sublime.

Photo from Lilly Pulitzer

Formalwear
Formal occasions are a chance for the Preppy girl to exhibit classic good taste. Simple, elegant dresses and separates from CK Bradley, Dakota Martin and J. Crew are good choices for the under-forty Prep, while older Preps favor Ralph Lauren Black Label, Valentino suits and, occasionally, Talbots.

Preppy Wardrobe: The Progeny of Prep

In order to truly understand the Prep wardrobe, we must consider its origin and influences. Preppy clothing is rooted in the past, but is chosen to suit the Preppy lifestyle. Prep style is restrained, conservative, and never tight or provocative. Most Preppy clothing is comfortable and durable, as Preps are very sporty and active. Preppy style is ageless and timeless, and true Prep means that a woman should be as comfortable in (subtly modified versions of) her ten-year-old daughter’s clothing or her seventy-year-old mother’s clothing as her own. No matter where the Prep is going (after all, even American aristocracy has to earn a living nowadays), she looks as though she could be on her way to the Maidstone Club or Larchmont Yacht Club.

Prep School Rumpled
Preps learn to dress themselves at boarding school, the first time that Mother isn’t around to lay their clothing out. Around this time, the Prep wardrobe evolves from freshly pressed button downs, sweaters and khakis to slightly wrinkled versions of the same. Prep school style remains a take on the old uniform, and only the shoes change: from Topsiders to 993s to Rainbows, depending on occasion and season. A game of touch football on the quad necessitates only a change into the 993s, while a cocktail-attire event is suited by simply slipping into a pair of well-worn boat shoes (never mind that Deerfield is about 120 miles from the nearest navigable waters), and an 80-degree day is celebrated by the donning of flip-flops (which can be worn in weather as low as twenty degrees Fahrenheit).
 

Photo from Ralph Lauren

English Country Style
Preps have been in close contact with their British brethren since the War or Independence, and as such, Preppy style is closely influenced by the Brits. Specifically, the English Country casual wear has an integral influence on the Preppy wardrobe.  Barbour waxed cotton outerwear, wool and cashmere knits, equestrian influence, and L.L. Bean rain boots and Hunter wellies all take their cues from the aristocrats over the pond. The Preppy Woman knows that if it’s good enough for the Her Majesty the Queen, it’s good enough for us.
 

Photo from Barbour

Boating Chic
The most American of the Preppy influences, Boating Chic can be thought of as the comprehensive conglomeration of preppy casual and recreational wear.  Boating Chic attire is machine washable, comfortable and often brightly or pastel-colored (the better to be seen in the dark, choppy waters during Block Island Race Week). This performance gear is the exception to the Preppy rule favoring natural fibers, for Preps love all manner of polyester fleece, nylon and rubber as long as it comes with a little Patagonia or Vineyard Vines label.

Photo from Vineyard Vines

The Updated Preppy Handbook: A Preppy Primer

The original Official Preppy Handbook, published in 1980, was written by a group of recent ivy-league graduates. A tongue-in-cheek guide written by the Preppy, for the preppy, it served as a style guide to a generation coming of age. As noted by one of the original Handbook’s co-authors in a 2005 New York Times piece, the popularity of preppy clothing has increased greatly in the last three decades. To some, Preppy remains a lifestyle and an ethos, not merely a polo shirt. This guide is intended as an homage to true Prep, not the Izod-and-Wayfarer-clad excess of the ‘80s, the Abercrombie-and-Fitch-sporting shopping mall culture of the ‘90s, or the self-conscious designer prep of the ‘00s. True Prep is classic, timeless and always in good taste. It is not flashy, showy, obnoxious or ostentatious; it is reserved, understated, simple and functional. True Prep is about continuity, tradition and grace.

Each of the authors was raised in a Northeastern preppy enclave and educated at an institution named in the original Preppy Handbook. We admit, however, that we are not immune to the lure of things that sparkle, the thrill of a beautiful dress or the ladylike feeling that comes from donning a decidedly-un-Preppy high heel on occasion. As children of the ‘80s, we were raised without a mold to cling to, and we have each defied expectations in some way. Yet we cling to the time-honored traditions of the Prep – quality above quantity, old above new, and functional over fussy – because they are in our blood and because they are, sometimes, our only compass as we navigate modern life.