Water repellency is often generated by taking advantage of surface textures and low surface energy coatings such as the one afforded by long perfluorinated side‐chains polymers. However, new regulations are phasing out these polymers because of their related health and safety hazard concerns. This is a particular challenge for water‐repellent fabrics as consumers expect safer products with stable performance and new functionalities. In this work, an approach is developed that allows for iCVD deposition of durable, conformal short fluorinated polymers stabilized with a crosslinking agent. As a result, high hydrophobicity and low liquid adhesion are achieved simultaneously while maintaining initial substrate breathability. It is explained why this polymeric coating—1H,1H‐perfluorooctyl methacrylate co divinylbenzene—exhibits remarkable hydrophobic properties amidst a wide range of other possible candidates. In order to further enhance the dynamic water repellency performance, the chemical treatment is combined with physical texturing—obtained through microsandblasting, a process particularly suitable for fabrics—thus making this combined approach a suitable candidate to meet the industrial needs. This work paves the way for the development of environmentally friendly, highly repellent coatings for large volume production and the application of roll‐to‐roll coating techniques, and multifunctionalization of fabrics and wearable devices. Initiated chemical vapor deposition (iCVD) of conformal short fluorinated polymers stabilized with a crosslinking agent is successfully carried out with 1H,1H‐perfluorooctyl methacrylate crosslinked with divinylbenzene. The ultrathin, grafted, and multifunctionalization aspect of iCVD leads to breathable, low material usage, durable, and EPA acceptable liquid repellent coatings particularly suited for substrates as diverse as fabrics, paper, and nanotextured silicon.