Best Bet: Sail Away

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Photo: Courtesy of My-Wardrobe.com

If there were ever a season to live in layers, it's winter. And insulation doesn't have to be big and bulky to keep you cozy. That's why we like the striped boyfriend sweater by Paul & Joe Sister. With only several strips of blue on the gray cotton cardigan, the nautical trend isn't too overpowering, and there are two modest bows on the front lower pockets to keep it flirty. Even better, the fit is loose enough to throw over your seasonal wears like thermals, turtlenecks, and long-sleeve tees. And bring it along in the hotter months, too — it looks great over a cami.

$112.20 at My-Wardrobe.com.