Order of positive mesomeric effect of halides
$\ce{2p-2p}$ orbitals overlaps better than $\ce{2p-3p}$, $\ce{2p-4p}$, $\ce{2p-5p}$. Although $\ce{F}$ is more electronegative, but it is also smaller in size. Both $\ce{F}$ and $\ce{C}$ (next to it) have $\ce{2p}$ orbitals to overlap.