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 LaurenEnglish 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 BarbourBoating 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