This dissertation looks at some of the most famous structures by talented and cryptic American architect Louis Sullivan (1856-1924) for fusions of Aesthetic Movement surfaces and two-part Classical Monumentality. For architects, the Aesthetic Movement allowed for a greater amount of freedom when it came to sources, massing, and ornament, which resulted in the creation of more highly textured surfaces than ever before. Under raking light, this texture produces some scintillating effects. Sullivan used this textural freedom throughout his career, creating some surfaces that sparkle. It will also be demonstrated that Sullivan changed his drawing style to better articulate his textural visions to others. The second way in which this dissertation looks at Sullivan’s architecture is through the lens of Classical monumentality, specifically that used in Donato Bramante’s Palazzo Caprini (constructed ca. 1512), which is better known today as the House of Raphael. Composed of a basement surmounted by a major order, Bramante’s venerable two-part pattern spawned legions of descendants. This dissertation will demonstrate that Sullivan applied lessons from derivatives of this structure’s facade to a range of building types. Visual analysis of select building facades will demonstrate that Sullivan kept combining these two themes throughout his career.