Diamond (pointed twill) and diaper (herringbone twill) woven assemblies are considered ideal for applications where thermal insulation, heat retention, wrinkle resistance, strength, softness, and breathability attributes are crucial. Limited research has been found on the optimization of thermal comfort and mechanical performance of warp face, weft face and balanced float diaper and diamond woven assemblies. In this work six different woven assemblies have been engineered using cotton (cellulosic yarn) on a dobby machine, having warp face (4/2) weft face (2/4) and balanced float (3/3) based diamond and diaper weave designs with equal number of thread densities. Thermal comfort (dry fluid transmission, thermal resistance, stiffness, and overall wet fluid management capability) and mechanical (tensile, puncture and tear strength) tests were performed for developed woven fabrics. The results of diamond warp face sample showed the highest dry fluid transmission and volume porosity. Diamond weft face specimens showed the highest thermal conductivity behavior and diaper weft face exhibited the highest overall wet fluid management capability behavior. Stiffness was the highest in diamond balanced float. Diamond warp faced fabric showed the highest tearing durability and diaper weft face showed the highest tensile resilience in mechanical performance attributes.