The design of multifunctional materials with tailored wetting and adhesion properties under different environmental conditions (dry or wet air, water, or extremely cold conditions/icing) is of paramount importance. It is still a challenging task to produce intelligent materials that are sticky/nonsticky only when it is desired. Controlled surface design based on the understanding of the effects of chemical functionality and polymer architectures can help to solve this problem. In this paper we report on the synthesis of adaptive PEG-PDMS brushes with different architectures (random copolymer and block copolymer) and investigation of their effect on the wettability and adhesiveness in wet and under water conditions. This study contributes to the development of materials with reversibly switchable and adaptive adhesiveness under controlled environmental conditions.