I always choose my clothes based on the character I'm playing - what suits them.
High on my list is my khajiit hunter's 'Savior's Hide'.
(Honorable mentions: glass, daedric, blades armor. I also like the 'tall boots', as opposed to the 'shoes' - don't remember the names. Thalmor would be nice if they had any unenchanted sets. Psijic looks cool too.)
When the skirt part was a bit longer or when it came with some sort of leggings it would definitely be the Savior's hide piece. For now I stick to the non bikini sleeveless Fur armour with fur boots and bracers, completed with some sort of golden necklace and a copper or golden circlet.
When it comes to metal armour it will be the Daedric one, although I don't like the fully closed helmet.
For robes/clothes I don't have a particular preference, depends more on my mood. Sometimes I see a woman in a nice one but I'm not rotten enough the kill her for it.