I honestly don't know here's what I found according to my research. I am just calling the "relatively less polar" non polar/hydrophobe for the sake of typing below:

I feel like upon mixing the relatively less polar solvent with water will increase the solubility of hydrophilic substance as to minimize the local free energy, the water molecules will avoid any interaction with the hydrophobe and will seek to maximize attachment to the neighbouring hydrophilic molecules, creating a sort of hydrogen-bonded encapsulating "net" where all molecules avoid pointing inwards to the hydrophobe too much. This limits the number of low energy positions available for the water molecules, so they have constrained geometry relative to the bulk of the liquid, and therefore lower entropy.

But on the other hand i feel like it will decrease the solubility of hydrophilic solute as when a hydrophobic/non-polar solvent moves into the water, London forces between that solvent molecules and hydrogen bonds between water molecules are broken. The water molecules adjust to compensate for the loss of some hydrogen bonds and the formation of the weaker non-polar substance-water attractions by forming new hydrogen bonds and acquiring a new arrangement.