I am amongst the group of cross dressers who is open about this to his wife. So, I invariably ask my wife if some top goes with a skirt or what shoes work with what dress, jewelry whatever., and while I get the occasional "Yeah, that works," more often than not, I seem to get "It depends," as an answer.
The subtlety of women's fashion is astounding. Wear a necklace over or under the collar? It depends. Skirt too short? It depends. Is it no wonder that we struggle with fashion?