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Preppy for me is all about summer. Think topsiders, seersucker and polos.

But how do you dress preppy in winter? Collegiate scarfs? Duffle coats? Sure. But what do you wear underneath?
 

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Tweed.
 

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For me, it's easier to be preppy in winter. Simply dress with the same casual precision as summer, except wear fabrics which are suited to winter. It may not be appropriate to wear Nantucket reds or madras shorts, but it is appropriate to wear a lime green sweater.

Thomas
 

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I only do preppy in spring to early autumn, 99% of my preppy stuff is RL. It probably is a case of changing to suit to winter.

swap:

Fair Isle vest sweater for a full sleeve Fair Isle sweater

light sweaters for dark shades

light patterned shirts (stripes, gingham, plaid, etc) for some dark colour like dark blue, red, dark green etc

no scarf option for wearing a college scarf

light jeans for darker jeans

cotton, linen or wool blazer for tweed or thick wool blazer



However, as Canadian as mentioned you cannot change everything. There some things like shorts that could not change for winter but could wear casual trousers.
 

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Layering!

turtlenecks (not folded over)
flannel shirts in tartan plaids
Shetland crew necks (alternately, LLB Norwegian, Fair Isle, argyle, etc)
Cords (preferably wide-wale), loden cloth, moleskins... flannel-lined chinos.
down vest or barn coat, Maine Hunting shoes...
 
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