The following manuscript presents the first attempt to fabricate and characterise electrospun polycaprolactone/poly(succinimide) composite meshes. While each material has its own advantages, a composite mesh could provide further options in the wide and diverse application spectrum of electrospun fibrous membranes. Polycaprolactone is a well-known polymer with excellent mechanical properties and a resistance against most chemicals. On the other hand, poly(succinimide) is an easily modifiable polymer that could provide functionalisation options to the system, giving rise to new and perhaps better alternative solutions, for example in the sensors field. Additionally, as both polymers are biocompatible and biodegradable the system could be an especially advantageous option in the environmental and biomedical fields as well. Three different meshes were produced by utilizing three different electrospinning configurations: a. Electrospun layered meshes, b. Co-electrospun meshes and c. Blend electrospun meshes. Physical-chemical (Attenuated Total Reflectance Fourier Transform Spectrometry, Scanning Electron Microscopy, Fluorescence Microscopy, Water Contact Angle), as well as mechanical characterisation, were performed validating the proof of concept for the three composite meshes. Furthermore, PCL/PSI meshes proved mechanically stronger as they exhibited almost double the loading capacities when compared to PSI only meshes. Wettability studies on the other hand proved that addition of a PSI component will decrease the water contact angle and therefore make the wettability nature of the composite meshes more favourable for biomedical applications.