How to Dress Preppy

From LoveToKnow Men's Fashion

It's often considered a foolproof style, so knowing how to dress preppy can be a real advantage for the fashion-challenged or those who just want to bring some variety to their wardrobes. Though the look is often considered trendy, in truth it is as classic as your favorite pair of worn in shoes.

Khakis and colorful tops are preppy essentials!

The Preppy Look

Preppy style automatically conjures up images of a privileged, elite few who may spend their free time at the country club, play golf, enjoy a little time on the yacht and boast an Ivy League degree. Yet, being a part of this world is hardly the prerequisite to successfully adopting a preppy style. Break down just about any preppy ensemble and you'll find that each piece is a classic; the pressed khaki pants, colorful polo shirts, crisp blazers and neat cardigans all define smart, clean clothing.

These are items that, no doubt, many men own and don't think twice about. Consider, then, that preppy dressing is more about how you wear the pieces than anything else. Worn untucked over a pair of jeans, that polo shirt is hardly representative of the traditional preppy look. Tucked into a pair of khaki shorts and with a sweater tied around its arms, though, it graduates to the culturally refined image that preppy style knows so well.

Preppy looks are unique in that they have a tendency to turn heads, but they aren't inherently eye-catching. There's nothing quite stunning about it, yet it looks so fresh and polished that one can't help but notice. Looking the part means adopting a few staple pieces that help define what it truly means to be preppy.

How to Dressy Preppy

Somewhere out there is probably a preppy manual that describes the look to the letter. No doubt men in the 1980s would gladly have taken every word of such a guide to heart; the preppy look was, after all, quite a phenomenon during that period. Today, though, men have the advantage of marrying classic traditions with modern sensibilities. The result is often a new sort of preppy style. It's one that remains true to preppy's inherent roots while embracing the present day's penchant for figure flattering cuts and even more flattering colors. Here are a few must-have items to get you started on the path to successful preppy dressing:

Polo shirts: You must embrace these to successfully go the preppy route. A selection of colorful polo shirts in shades like kelly green, bright pink, vibrant yellow, blue and purple are essential.
Sweaters: Cotton or cashmere cardigans, vests, crewneck and v-neck sweaters that fit well are necessities. Don't make the mistake of going the baggy route; these sweaters should fit just right. When in doubt, slightly larger is better than slightly smaller!
Button down shirts: Just as essential as the polo shirt, an oxford button down shirt is more appropriate for dressy occasions. Again, think color and a great fit.
Chinos: No preppy wardrobe is complete without a pair (or two) of chino pants. They wear well from the office to the golf course, and they're available in plenty of colors. Khaki is particularly versatile.
Jeans: Yes, jeans have a place in the modern preppy male's wardrobe. Perfect for occasions when khakis somehow aren't casual enough, a pair of slim, straight cut jeans does the job nicely. Fold the cuffs up for an even preppier look.
Sport coats: If you're envisioning a crest-emblazoned, fitted blazer right about now, you're on the right track. The crest is not essential, but a good fit certainly is.
Shorts: Pleated, chinos, cargos – opt for any of these styles, which all pair perfectly with everything from a button down sport shirt to a polo shirt.
Jackets: During spring, a light windbreaker that fits like a glove over your top works well. Weather-resistant pullovers are perfect for cool days on the golf course or boat.
Coats: During fall and winter, make the switch to richer materials – tweed is a great choice. Wool pea coats are also ideal because they keep you warm and look classic paired with a scarf, pullover sweater and jeans.