Gitman Vintage Hopsack Plaid Shirt in Blackwatch
Buy It Now at Indigo & Cotton, $172

Tartan is everywhere during the holidays, but blackwatch is especially present. Sure, you could go whole hog in a blackwatch suit, but a shirt is more versatile and likely for you to wear all season long. Gitman Vintage is known for their balance of quality and fit, and this blackwatch shirt is just about perfect for wearing tucked or untucked, with a cut that's slim but not super tight.