The perfect time to shoot: the golden hour. I used to disagree and I thought the best time to shoot was when the sky is overcast (which is still good), until my boy/photographer brought the photos to life!
The golden hour is the hour before sunset or after sunrise. This is the perfect time to backlight your photos, it makes them seem almost magical! Also, if you're shooting fashion content, wear warmer tones in your clothing to mirror the colouring of the sky.
Tips From Experience:
Shoot Fast: You only have approximately one hour, don't waste any time!
Plan Ahead: Know your location, outfit and shots you want (roughly) ahead of time.
Behind The Camera: The photographer will know how to adjust his/her camera accordingly.
Dress: Zara, Turtleneck: Forever21, Boots: Call It Spring