Two bodies of law govern what a building looks like from the street, and they pull in opposite directions. This article explains historic preservation law — how designation happens, what a certificate of appropriateness actually reviews, why the takings challenge almost never works after Penn Central, and how the federal Section 106 process reaches projects that have nothing to do with the federal government until a permit or a dollar appears. It covers the rehabilitation tax credit that makes many preservation projects financially possible and the certification requirements that decide whether it is available. It then turns to sign regulation, where the First Amendment constrains local government in ways preservation law does not, and traces the doctrine from Metromedia through Reed and City of Austin. It closes with the collisions between the two systems, the honest criticisms of preservation as practiced, and what an owner facing either regime should actually do first.