Still learning: My ongoing odyssey with belts

Here is one of my major style challenges: I really want to become one of those women who understands belts—the ones who wear them over dresses or peeking out under a pretty shirt on a pair of jeans, and it all looks effortless and cool, not contrived and dorky. I think maybe the problem is my belts themselves. I've never really invested in a good one—this is embarrassing, but two of my three belts require the aid of carefully positioned duct tape to keep the ends from flailing away from my body. Another problem is I have no idea what to look for: Do I go trendy and colorful like this woven style? Or should I try something clean and classic like this one from Ralph Lauren? Is this '70s ring style really as "killer" as the auction claims? Or would I look sexier in a wide version, which kind of appears to be modeled by Kimberly Stewart?