Nobody cares about Dante smoking. At least, nobody should. Smoking is not meant to look 'cool', and it doesn't. However, I'd think it were cooler if he continued smoking despite what people tell him to do. I feel this way because people who tell others what to do, what to eat and what to consume deserve to get slapped in the face for being dictatorial s*itheads. Everybody knows smoking is unhealthy; you're not helping the smoker by nagging all the time, nor did the smoker ask for help.
And about Dante's look, I hated it because there's not really a reason for him to look like that. You say he's poor. Sure, true. However, the simple fact is, NT decided this was what Dante should look like. They could've made him a little bit more affluent. Although, I guess that's not even the point. You could argue the old Dante probably didn't have a lot of money either (in the games, at least), yet he looked cool and well-groomed and all that. The fact is, NT made him look like this because it was their view of what his image should be like. The clothing isn't there just to illustrate that he's poor or something; this is a character we're talking about, and his clothes represent his character, just like Vergil's clothes sort of represent what he's like. In DMC3, Dante wore no shirt beneath his trench coat. This was a conscious decision Capcom made, not a decision Dante made to look extra 'sexy' or something. I think Dante looks 'meh' in DmC; nothing like a hero (which I suppose was the point), but he also doesn't look cool. He just looks... ordinary, and that doesn't scream 'Devil May Cry' to me. When he uses the DT, he does look a bit less ordinary, but still pretty boring, I think. The DT should've been a way to show his true form; to show what he's really like and how awesome he supposedly is inside. Just my opinion.