I like guys who's pants are pulled up and yeah, most of the guys I know wear belts, leather, often custom-tooled. Usually with a belt buckle. A guy with a fancy belt gets passed, that screams rodeo cowboy/wannabe and those are often bad news. Shirt tucked in, well fitted jeans, that looks good to me. Then again, I date farmers, mechanics and country boys. They all wear jeans, plaid shirts and belts.
probably not. I haven't really updated my belts too much but I improved the rest of my style a lot over the past year and it does not change how many women hit on me or anything. Best thing that could happen is a girl would already like you for some other reason and belt would be good in that it would be a way for her to break the ice and start conversation with you asking about your belt. Not much else though.