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In the winter, you'll want to layer underneath your overalls simply to start with a foundation of warmth. While you can always add a jacket on top à la Bieber, a thick turtleneck sweater is a great starting point. Once you add the overalls, you can cinch your waist with a belt or two if your layers are feeling bulky around the bodice. Timberland boots make for functional footwear that also allow for a tuck of the pant leg if it's wet outside.