Textiles are used for many different applications and require a variety of properties. Wet functionalization improve textiles’ properties, such as hydrophilicity or antimicrobial activity. Chitosan is a bio-based polymer widely investigated in the textile industry for this purpose. A weaving comprising a cotton/polyester mix and a pure-polyester weaving was functionalized with different concentrations of chitosan to determine the most robust method for chitosan detection in both cotton- and polyester-containing materials. Additionally, mixtures of chitosan with 3-glycidyloxypropyltriethoxy silane (GLYEO) or 3-aminopropyltriethoxy silane (AMEO) were applied in a one-step or two-step procedure on the same fabrics. Scanning electron microscopy (SEM) combined with energy-dispersive X-ray spectroscopy (EDS) and dyeing with Remazol Brilliant Red F3B demonstrated the presence of chitosan and silanes on the textiles’ surfaces. While non-functionalized textiles were not stained, the dependency of the dyeing depths on the chitosan concentrations enabled us to infer the efficacy of the very short processing time and a mild dyeing temperature. The one-step application of AMEO and chitosan resulted in the highest presence of silicon on the textile and the greatest color intensity. The functionalization with GLYEO reduced the water sink-in time of polyester, while chitosan-containing solutions increased the hydrophobicity of the material. Washing experiments demonstrated the increasing hydrophilicity of the cotton/polyester samples, independent of the type of functionalization. These experiments show that chitosan-containing recipes can be used as part of a useful method, and the type of functionalization can be used to adjust the hydrophilic properties of polyester and cotton/polyester textiles. Via this first step, in the future, new combinations of bio-based polymers with inorganic binder systems can be developed, ultimately leading to sustainable antimicrobial materials with modified hydrophilic properties.