During this study four different methods of hydrophobization of cotton textiles via thiol-ene click reaction were compared. It was hypothesized that the same products would be obtained in all cases, albeit in different ways. During synthesis of hydrophobic compounds 2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane (D4Vi), (3-mercaptopropyl)trimethoxysilane (M) and alkyl thiols of various alkyl chain lengths (C6H13SH(C6), C8H17SH(C8), C10H21SH(C10), C12H25SH(C12), C18H37SH(C18)) were used as a substrates. Some of the modifiers were synthesized via thiol-ene click reaction and then introduced to the cotton textile via a sol-gel process. The remaining modifiers were synthesized via thiol-ene click reaction directly on to cotton textiles. The influence of alkyl chain lengths on the hydrophobic effect were also investigated. Hydrophobization of cotton textile was evaluated through measurement of water contact angle. Additionally, the surface of the cotton textile was also examined via infrared analysis, scanning electron microscope (SEM), and elemental analysis (SEM-EDS). As a result of this study a superhydrophobic cotton textile was obtained. The research showed the significant influence of the type of modification method via thiol-ene click reaction on the hydrophobicity of cotton textiles.