My analysis focuses on the journals of Alejandro Malaspina titled, Alejandro Malaspina: En busca del paso del Pacífico (1990 edition), written during his expeditions to the Pacific Coast of California and the Northwest (Alaska) in 1791, and the diary of Fray Pedro Font edited and translated by Herbert Eugene Bolton as Font’s Complete Diary of the Second Anza Expedition. The edited and translated volume was first published in 1930 and reissued in 1966. The Font diaries record the day to day events transpiring during Captain Juan Bautista de Anza’s expedition in Arizona and California (1775- 76). The study has two sections: Section I focuses on Malaspinas’ journals while Section II is devoted to some aspects of Font’s Diary related to the clothing or lack of clothing worn by the Indigenous peoples. The essay deals specifically with issues of Spanish responses to indigenous lack of clothing (nakedness) or their distinctly different way of dressing (the berdaches). I highlight how the Spanish/Indigenous encounters veer from the comical to the tragic and posit that the encounters are characterized by the dialectic of “naked” and “clothed.”