Hydrophobicity is an important feature in medical applications. Reentrant structures are used to achieve this functionality on the surface to the greatest extent possible. This study provides a simple and cost-effective approach to producing these structures without the use of nanoparticles and fluorine-based coatings that can make this approach applicable to medical devices. This was done by indirect 3D printing using a low-cost commercially available Fused Deposition Modelling (FDM) printer. The FDM printer is used to create a mold with a top layer of straight lines separated by a gap. Polydimethylsiloxane (PDMS) is cast into it negatively replicating the mold surface to make the reentrant structures. As a result, a functionalized surface with the reentrant wall structure having an edge angle of 121° ± 10° was created with anisotropic wetting reaching an optimal static contact angle of 160.3° ± 2.9° with the lowest rolling angle of 29.2° ± 4.2° for a 10 uL water droplet.