Compression garments are extensively used for various therapeutic treatments and are expected to deliver accurate and reproducible compression pressures. This study focuses on developing an analytical model to predict the pressure generation by compression garments on human limb analogues. The analogues consisted of non-compressible and compressible cylinders that were chosen as the first step towards evaluating pressure generation on real human limbs. An experimental platform was developed to quantify the relationship between material properties, initial garment extension and pressure. A mathematical model was presented that provided greater accuracy in predicting the pressure generated by compression garments than the existing Young-Laplace equation for compressible limb analogues.