Long before Blair Waldorf and Chuck Bass were strutting around the Upper East Side, the preppy look was highlighted in '80s movies such as Sixteen Candles and The Breakfast Club. Even farther into history, “prep” was a term used to describe uniforms worn at preparatory schools. The style that traditionally represented conformity and exclusivity has changed over the years. Lisa Birchach’s, Preppy Handbook democratized the preppy look. Because of this, J Crew, Lacoste, Polo Ralph Lauren and other preppy brands reached new levels of popularity during the 1980s.

More recently, the preppy look has made a comeback in a more comfortable, vintage way. This Fashionista’s Rugby button up is classic, but still looks young tucked into her brown skirt because of the purple color and fun pattern on the collar. Her modern sunglasses, brown Timberland pull on boots and brown leather bag give her a more casual vibe and personalize her look.

Ready to put some prep in your step? Stock up on blazers, boat shoes, polos and basically anything sold at Vineyard Vines. Incorporate your own style with funky accessories or bag.   

Hint: Dressing preppy is also a great way to experiment with menswear/menswear inspired clothing.

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