Men's Fashion Experts...I need help :D?

I'm looking to go into a more luxurious, expensive look.. Do boots look good on men this winter (like Ugg and Prada, no North Face or Timberland)? I want a fashionable boot but not a sporty looking one? What kinds of footwear do you suggest? Also, what kind of pants should I wear? I don't want to buy too much gray (since it's in this season) because I'm not sure if it'll be in for Spring/Summer next year. Help :D