Your pupil is functionally the same as the aperture on a camera. Whenever light passes through an aperture, there is some diffraction that happens to it; the angle of the light changes. This is separate to anything the lens does. If there's too much diffraction, you won't be able to tell two different sources of light apart. The amount of diffraction depends on the wavelength of the light and the size of the aperture. Bigger apertures and shorter wavelengths diffract less. This "diffraction limit" has a formula accordingly.

So for the question, we make some basic assumptions: take the wavelength of red light as it's the longest wavelength for visible light, and assume he needs to be able to tell apart two light sources 2 metres apart at a distance of 15 miles to distinguish individual riders. We figure out the angle between two points 15 miles away and 2 metres apart and now we know the angular resolution necessary. We know that the diffraction limit of Legolas' eyes has to be at least as small as that resolution. We also know our wavelength, so we can stick those into the formula and find out the minimum aperture (ie, the minimum diameter of Legolas' pupils to make out the riders at that distance)