In contrast to larger flight-capable insects such as hawk moths and fruit flies, miniature flying insects such as thrips show the obligatory use of wing–wing interaction via “clap and fling” during the end of upstroke and start of downstroke. Although fling can augment lift generated during flapping flight at chord-based Reynolds number (Re) of 10 or lower, large drag forces are necessary to clap and fling the wings. In this context, bristles observed in the wings of most tiny insects have been shown to lower drag force generated in clap and fling. However, the fluid dynamic mechanism underlying drag reduction by bristled wings and the impact of bristles on lift generated via clap and fling remain unclear. We used a dynamically scaled robotic model to examine the forces and flow structures generated during clap and fling of: three bristled wing pairs with varying inter-bristle spacing, and a geometrically equivalent solid wing pair. In contrast to the solid wing pair, reverse flow through the gaps between the bristles was observed throughout clap and fling, resulting in: (a) drag reduction; and (b) weaker and diffuse leading edge vortices that lowered lift. Shear layers were formed around the bristles when interacting bristled wing pairs underwent clap and fling motion. These shear layers lowered leakiness of flow through the bristles and minimized loss of lift in bristled wings. Compared to the solid wing, peak drag coefficients were reduced by 50–90% in bristled wings. In contrast, peak lift coefficients of bristled wings were only reduced by 35–60% from those of the solid wing. Our results suggest that the bristled wings can provide unique aerodynamic benefits via increasing lift to drag ratio during clap and fling for Re between 5 and 15.