Not only is this a tumblr curated with excellent taste. Not only are the situations it addresses complicated to the extreme. But the reasoning? Extremely detailed.
What to Wear When, which is a project of tumblr Rave Sashayed and includes Polyvore boards, is a tumblr that answers the important questions like "WHAT TO WEAR WHEN: You Accompany A Rugged, Gorgeous Doofus Archaeologist Into a Possibly Treasure-Hunting/Life-Endangering/Romantic Situation," "WHAT TO WEAR WHEN: You Are An Evil Queen Donning the Full Regalia," and "WHAT TO WEAR WHEN: You Are A Stylish Dwarf Princess Reclaiming Her Lost Home From A Dragon." The advice on this blog is invaluable. Two of my personal favorites are below, but seek out the whole thing.