In nature, many swimming and flying creatures use the principle of oscillatory lift-based propulsion. Often the flapping element is flexible, totally or partially. The flow dynamics because of a flexible flap is thus of considerable interest. We are interested especially in lunate fish propulsion. The present work investigates the effect of trailing edge flexibility on the flow field created by an oscillating airfoil in an attempt to mimic the flow around the flexible tails often found in fish. A flexible flap with negligible mass and stiffness is attached at the trailing edge of NACA0015 airfoil. The flap length is 75% of the rigid chord length. The airfoil oscillates about a hinge point at 30% chord from the leading edge and at the same time it moves in a circular path in stationary water. The parameters varied are frequency, amplitude of oscillation and forward speed. For a given combination of amplitude and frequency of oscillation, the forward speed is chosen such that the Strouhal number comes around 0.3, which falls in the gamut of Strouhal numbers for maximum propulsive efficiency. We visualize the flow with dye and particles and measure velocities using Particle Image Velocimetry (PIV). We use shadow technique and image processing to study the flap dynamics. We do a qualitative and quantitative comparison of the wake flow generated by two airfoil models, one with rigid trailing edge (model -B) and the other with flexible trailing edge (model -A) i.e. with a flexible flap fixed to the trailing edge. We study the flap dynamics, the flow around the flap, evolution of vortices, wake width, circulations around airfoil and vortices, momentum and energy in the wake (which is measure of propulsion efficiency), vortex geometry in the wake in terms of vortex spacing, etc. We also conduct a parametric study for both the models. Flap dynamics plays a prominent role in defining the signature of the wake. The observed flap deflections are quite large and the flap exhibits more than one mode of deflection; this affects the vortex-shedding pattern. The flap tip also executes a near sinusoidal motion with a phase difference between the trailing edge and the flap tip. The dye visualization studies show that a flexible trailing edge induces multiple vortices while in case of a rigid trailing edge, large vortical structures are shed. In case of flexible trailing edge (model -A), the vortices are shed away from the mean path of motion and are arranged in a ‘reverse Karman vortex street’ pattern producing an undulating jet representing a thrust on the airfoil. For the same Strouhal number, in case of rigid trailing edge (model -B), the vortices are shed nearly along the mean path of motion indicating a momentumless wake. The wake structures, particularly in case of model -A, are nearly insensitive to variations in amplitude and frequency. The wake of model -B shows some variable flow patterns for different amplitudes of oscillation. Although the total chord of model -A is 1.75 times more than the chord of model -B, the wake width is nearly the same for the two models when the amplitude of oscillation is same. The addition of the flap to the airfoil keeps the wake flow two-dimensional or symmetric about the center plane for longer times and longer downstream distances in comparison with the wake flow generated by rigid trailing edge. For 15o and 20o amplitudes of oscillations, the flow separates over the airfoil itself; the interaction of the separated flow with the flexible flap is quite interesting, which needs further investigations. The wake generated by the airfoil with flexible flap at the trailing edge has some common features with the wakes generated by the flow over a flapping filament (which is the one-dimensional representation of a fluttering flag), an accelerating mullet fish (a carangiform swimmer) and a steadily swimming eel (an anguilliform swimmer).