Ask the Fashionista

What are some ways I can wear a pair of black, mid-length cowboy boots without looking like a complete cowgirl?  
How do I dress for a date if the guy hasn't given me an indication of where we're going or what we're doing?
So here is the deal: I am in love with tights. See: this look and this look. — I'm in love.
I love my Tory Burch flats, in part because of the elastic on the back that makes them more comfortable. Are there any other nice — but not as expensive flats that have this sort of backing?
I just got green cargo skinny pants. Is this on trend for the season? What kind of shoes and tops should I be pairing these with? 
What kind of boots should I invest in for the fall? I'm looking for something trendy, yet practical to wear to class.