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How to Dress Preppy

Dressing preppy is a classic style that always looks flawless and timeless. If you have a preppy wardrobe, you can wear it anywhere and look sophisticated and well put together. To dress preppy, there are several signature pieces that you need to have in your wardrobe.


The classic preppy shirt is the polo shirt. The polo shirt is worn buttoned up most of the time but it can be worn with one button unbuttoned at the top. An oxford shirt is also appropriate for the preppy look. You can wear these long-sleeved or short-sleeved and in just about any color. The most common colors in the preppy look are white, red, blue or green. Pastel shirts are also appropriate for the look.

Sweaters and Blazers

A cardigan or button-up sweater is perfect for the preppy look. The sweater should be kept with you even if it isn’t cold enough to wear it. You can lay the sweater over your shoulders and lock the cuffs around your neck to hold it in place. You can also tie the sweater around your waist with the sleeves in the front for a casual event.

If you do want to wear the sweater, button it up. Make sure the collar of your shirt is showing above the collar of the sweater. Shirts and sweaters should go together in light colors such as a white shirt and a yellow sweater or a pink shirt with a white sweater.

Blazers are also a classic part of the preppy look. Blazers, particularly in tan or beige, will perfect complement any preppy outfit. A blazer can be worn over anything, including over a sweater. A blazer that has patches at the sleeves is a great preppy look. But even without patches, a blazer looks great with a preppy shirt, sweater, pants or skirt in neutral tones.

Pants and Skirts

Khaki and tan are the perfect preppy colors for skirts and pants. A pencil skirt in khaki is perfect with a white button-up shirt and a yellow sweater. Dockers or other tan pants are another great preppy look. They can be paired with a polo shirt for casual occasions and with a dressy shirt and sweater for more formal ones. The pants should be pressed and should have a visible crease on each side.

Plaid, in moderation, is also a great preppy look. Short plaid skirts along with starched white shirts are a classic preppy outfit. Plaid pants are generally not consider preppy, but a plaid scarf or a plaid shirt under a solid colored sweater will work beautifully.


The classic footwear for a preppy outfit is loafers. Penny loafers, loafers with fringe and plain brown loafers are the ideal shoes to wear with a preppy outfit. Be sure to wear socks in a neutral color along with the loafers. White socks or a pastel color will go well with the neutral tones of the outfit. The socks should be ankle socks that are folded over neatly and precisely. All aspects of the outfit should stay clean and pressed at all times.

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