Insect herbivory is a dominant interaction across virtually all ecosystems globally and has dramatic effects on plant function such as reduced photosynthesis activity and increased levels of defenses. However, most previous work assessing the link between insect herbivory, photosynthesis and plant defenses has been performed on cultivated model plant species, neglecting a full understanding of patterns in natural systems. In this study, we performed a field experiment to investigate the effects of herbivory by a generalist foliar feeding insect (Lymantria dispar) and leaf mechanical damage on multiple leaf traits associated with defense against herbivory and photosynthesis activity on two sympatric oak species with contrasting leaf habit (the evergreen Quercus coccifera L. and the deciduous Quercus pubescens Willd). Our results showed that, although herbivory treatments and oak species did not strongly affect photosynthesis and dark respiration, these two factors exerted interactive effects. Insect herbivory and mechanical damage (vs control) decreased photosynthesis activity for Q. coccifera but not for Q. pubescens. Insect herbivory and mechanical damage tended to increase chemical (increased flavonoid and lignin concentration) defenses, but these effects were stronger for Q. pubescens. Overall, this study shows that two congeneric oak species with contrasting leaf habit differ in their photosynthetic and defensive responses to insect herbivory. While the evergreen oak species followed a more conservative strategy (reduced photosynthesis and higher physical defenses), the deciduous oak species followed a more acquisitive strategy (maintained photosynthesis and higher chemical defenses).