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Winter Fashions for Boys

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The Preppy Look for boys made a comeback a few years ago and is still going strong for Winter 2008-2009. The basics of this look never change, but the fits, colors and unexpected graphic prints are updated for a modern and casual look that is ideal for school or just hanging out looking cool. This year's Preppy Look is more casual and infused with personality.

What He'll Need for the Look

Polo Shirts and Rugby Shirts

Winter Fashions for Boys
polo.com
It's as popular as ever, and even better than you remember. The classic Polo shirt can now be custom made from his favorite colors for a look he'll love. Visit polo.com, and in four easy steps, you can design your very own Polo shirt.
Or just hit the stores and choose polos or rugby shirts in his favorite colors. Rugby shirts are great because they are always in style, effortlessly dress up or down, and come in an amazing array of colors and patterns to suit many different tastes.

Buy Direct: Orange Multi-Stripe Rugby at polo.com

Classic Button-Down Shirt

Winter Fashions for Boys
gapkids.com
A classic button-down shirt is a Preppy boy's essential. He'll need one in basic white as well as a light blue one, but don't forget more exciting alternatives like striped, checked and plaid shirts. Don't be shy with color; boys look great in pink, light blue, greens, yellows, purples and any other color you can imagine. To modernize his preppy look, layer his button-down under his ruby or polo.

Buy Direct: Blue Tartan Plaid Shirt at gapkids.com

Blazer

Winter Fashions for Boys
gapkids.com
Sure, he can get classic and don a standard blazer, or he can funk up his modern preppy look with a retro-inspired blazer. For a funky winter look, layer a blazer over a hoody or zippy.

Buy Direct: Herringbone Blazer at gapkids.com

Trousers and Jeans

Winter Fashions for Boys
oldnavy.com
In the past, The Preppy Look demanded crisply-ironed trousers. Now, choose more casual pants such as chinos, cotton pants or even a nice pair of dark washed jeans. Go with basic colors on the bottom like tan, brown, navy and grey.

Buy Direct: Plain Front Khakis at oldnavy.com

Classic Footwear

Winter Fashions for Boys
zappos.com
For a more traditional Preppy Look, choose a pair of athletic shoes by classic "preppy" brands like Lacoste or Ralph Lauren. Or get more modern and choose a pair of hybrid dress-athletic shoes. In the witner, you can't go wrong with a pair of neutral colored boots.

Buy Direct: Ugg Kids Birch Boot at zappos.com
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