If you were to map out the intersection of preppy style and Christmas cheer, you'd probably land right on richly-toned plaids. The classic print feels just right at the holidays, but it's understated enough to fit right in at a cocktail party or even at church on Christmas Eve. Mary Janes // Booties // Pumps I curated these favorite pairs because they are budget-friendly and can go seamlessly from day to night. Plus, each of these comes in several different colorways. If deep reds, blues, and greens aren't your style, these shoes come in colors like soft neutral grays or even brighter patterns with more yellow in the fabric. These pairs can elevate jeans to date night attire or turn a plain dress into a festive outfit. As an Amazon Associate, I earn from qualifying purchases.