When is it the best time for a portrait session?
It all depends on your location choice and what the weather is like on the day of the shoot. But preferable location sessions are done closer to sunset.
Should we wear matching clothes?
No, but ensure that the outfits have matching colour schemes. The clothes should not have any branding on and stay away from bright colours, patterns and pictures. Soft natural colours are the best, but pure white should be minimal.