It seems that the natural transition is to layer up, go matte with makeup and embrace boots.
The top articles to help you with this transition?
How To: Transition Your Makeup bag from Summer to Fall from Makeup.com
4 Tips: Summer to Fall Fashion from GirlsGuideTo
How To Transition Your Makeup from Summer to Fall from The Life of the Wife
Summer to Fall Maxi Skirts from Deborah Simmons
How do you deal with the transition after months of warm weather? What pieces do you keep, and what pieces do you swap out?