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You can absolutely wear your pencil skirt — don't let the chill stop you. Instead, be prepared with tights underneath and two cozy layers on top. Start with a festive jacquard or embellished sweatshirt up top and bundle up with a cool-girl leather jacket for contrast. If you fear being underdressed, just add in more sparkle with a pair of jeweled earrings or go for even more shimmer with a statement necklace.

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