The aim of this article is to determine experimentally and numerically the influence of material degradation on the deformation of a paraglider during flight. The presented method regards numerical modeling of pressure distribution over the wing and its effect on paraglider behavior; the considerations are preceded by experiments on three types of Polyamide 6.6 paraglider fabrics, subjected and not subjected to thermal, UV and flexing degradation. Scanning electron microscope (SEM) records allowed to determine the structural characteristics of the analyzed samples. Air permeability and mechanical tests are the input data for the computational simulations. When a pressure drop of 200 Pa is applied, all the analyzed samples are impermeable, except for those damaged by flexing. Thus, flexing damage has the greatest influence on the air permeability change among all considered aging factors. Aging caused by UV radiation has the greatest influence on mechanical properties. No major influence of thermal ageing on the mechanical properties of the considered samples is observed. Safety factors of the considered materials not subjected to degradation range between 3.94 and 6.00. Safety factor of fabric no. 1 subjected to the UV degradation is equal to 1.33; this result does not secure a safe usage of the considered material. The methodology described in this research can help to predict paraglider covering materials’ behavior in flight; it assumes many cases, i.e., applying a new material or the material at any point of its life cycle. Thus, the practical implications of this model supported by numerical methods may result in saving time and cost in producing prototypes, as well as potentially assessing the safety of used wings. Future research activity can introduce the application of different elastic–plastic damage models to determine the paraglider behavior during collapse.