Bending stiffness is an important property of textile materials, especially from the point of view of the utility comfort of the clothing user. The stiffness of fabrics determines their ability to create folds under the influence of gravity. At the same time, it influences the aesthetic effect of clothing usage, in particular its fitting to the user’s body. Fabric stiffness is also important from the point of view of the sensorial comfort of clothing usage. In the work presented seersucker woven fabrics of different structure were measured in the range of their stiffness. The fabrics investigated differ from each other in the aspect of the repeat of the seersucker effect and linear density of weft yarn. Measurement of bending stiffness was performed using two measurement methods: Peirce’s Method (Fabric Stiffness Tester) and an MOO3F Digital Pneumatic Stiffness Tester. On the basis of the results, an analysis was performed to assess the influence of the repeat of the seersucker effect and linear density of weft yarn on stiffness parameters determined using both methods. Results confirmed that the linear density of weft yarn and the repeat of the seersucker effect influence the bending stiffness of fabrics determined by both testing methods applied. Some problems resulting from the surface geometry of the seersucker woven fabrics were indicated and discussed.