Q&A: Shoe Rules?

Tribeca - Prime Factor (Brown Plaid) - Women's  I’m having shoe issues. I have recently gotten “into” shoes  more and more the past year or so, and I’m stumped. I have a few  questions…

1. How do I wear patterned shoes? I keep seeing these great plaids  and other patterns on shoes, but I’m not confident about what outfits  to wear them with, so I never buy them.   But I’d love to! Help!
 
2. What are the rules about wearing stockings with peep-toe pumps? I  feel that there are only so many situations when you can go with bare  feet especially for business and dressing up, but I’m not sure how to  wear hose with this style shoe. Yes hose? No hose? Match the shoes  with the hose? Help! ~Monica

Readers, what are your thoughts?!?