AbstractBio‐inspired unidirectional flow of tiny aqueous droplets across the fibrous substrate paved the way for the emergence of various advanced materials. In the past, textiles decorated with noncontact‐based wettability‐patterns enabled unidirectional water flow—without flooding the top surface by the transferred water. However, such approaches mostly suffer from a low (≈0.176 µL mm−2 s−1) flow rate and are likely to delay the overall liquid ejection process. Here, a chemically reactive coating capable of tailoring water wettability (121.3° ± 2.4° to 153.3° ± 1.8°) is introduced on commercially available textiles to develop chemically modulated wettability‐pattern for achieving a rapid (2.57 ± 0.28 µL mm−2 s−1) flow rate of water against the gravity with an ability to roll the accumulated liquids on the top surface. The spatially selected and controlled chemical modification with hydrophilic and hydrophobic small molecules through a 1, 4‐conjugate addition reaction yielded a 3D channel with a customized wettability gradient. The pinning and depinning of invaded water through such chemically decorated channels enabled unidirectional and fast penetration of liquid, where the water penetration resistance largely depends on the water penetration direction and dimension of the chemically modulated channels.