Exfoliation of layered materials provides nanosheets, such as monolayers and few-layers. In recent years, nanosheets have attracted much interest as two-dimensional (2D) materials for their diverse properties and applications originating from the anisotropic characteristic structures. Exfoliation methods have been developed depending on the types of interactions between the layers, such as van der Waals and electrostatic interactions. The present review focuses on exfoliation chemistry based on rigid and soft natures of the layered materials. The rigid inorganic layered compounds are converted to the soft layered materials with interaction of organic guests. The surface-functionalized nanosheets are obtained by exfoliation of the soft layered composites with dispersion in organic media. The exfoliation behavior is governed by the flexibility of the precursor layered materials, i.e. interaction between the interlayer guest and dispersion medium. Although exfoliation is generally an uncontrollable top-down process, materials informatics on our own experimental small data assists elucidation of the control factors toward tailored 2D materials. The exfoliation schemes are applied to a variety of layered materials. The present review shows potential new insights for exfoliation chemistry of soft layered materials.