Colloidal self-assembly is widely exploited to fabricate complex materials using the bottom-up approach and is useful in numerous applications. Colloidal crystals assembled through the self-assembly route can have long-range order and mimic a wide range of physical properties displayed by their atomic counterparts. Our interest lies in a particular class of colloids, namely, soft colloids, which show intermediate behaviour between polymers and hard spheres. Here, we study the evaporative self-assembly of amphiphilic soft colloids composed of poly (N-isopropyl acrylamide) (p-NIPAM) microgels. The spontaneous adsorption of soft colloids onto the air/water interface and the associated conformational changes of colloids are exploited to generate a loosely-packed monolayer of particles with hexagonal symmetry. The role of polydispersity and the softness of the interparticle interaction potential on the ordering of the colloids are investigated in detail. In addition, the temporal evolution of viscoelasticity of a skin-like particulate layer formed by the adsorption and deformation of the soft microgel particles to the air/water interface is measured using the multiple-particle tracking microrheology technique. The microgel particles that behave like colloidal surfactants are successfully used to tune the contact line dynamics of evaporating drops to such an extent that a sessile drop stays pinned onto a hydrophobic substrate for the entire duration of evaporation. The adsorption of these soft particles onto the air/water interface is also found to modulate fluid flows within evaporating drops and form prominent depletion zones in the dried deposits. Notably, the width of the depletion zone is found to increase linearly with the volume of the drop and is understood by a simple scaling argument.