Have you ever heard of the "Golden Hour" in photography?  The golden hour is considered the best time of day to take outdoor pictures.  It is the hour right before sunset or after sunrise, approximately.  The reason the light is so wonderful during the golden hour is that the sun is low in the sky creating diffused light.  This type of lighting does not create harsh shadows that can give dark circles and cause squinting.  In fact this type of light acts like a filter minimizing wrinkles and smoothing skin. 

The only reason not to schedule a photo-shoot at this time, in my opinion, is if you have little ones that are not happy at one of those times.  I just did a 7AM photo shoot for a family celebrating their little one's first birthday.  Although sunrise is at 5:30AM these days, 7AM was still early enough.  We worked in open fields at first and then went to open shade. What is open shade?

Open shade it the large shadow of a building or under a few trees with good coverage.  If you can not be out taking photos in the golden hours, which is fairly limiting, then look for open shade.  Just be careful that you are not standing in speckled light on your face.  That is unflattering in photos.

Here are a few example photos of my girl.  They are taken on the same day at noon, mid-afternoon and the golden hour. I think the difference is pretty clear.