The conformations and planar chirality of macrocyclic hosts are of great importance because of their large influence on the complexation abilities and selectivities of the host molecules. Pillar[n]arenes are a class of macrocyclic hosts that have attracted great interest over the past decade since the first example was reported by our research group. Because their phenylene units are connected by methylene bridges at the para-position, pillar[n]arenes have abundant conformational and planar chiral stereoisomers in principle. In this review, we provide an overview of the conformational and planar chiral properties of pillar[n]arenes and their applications.