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.