Yes, I know those shoes. I used to have a nice pair of steel-tipped Timberlands I'd wear everywhere... those things were monsters. But your feet sure were safe in there.
I realized after a while though that dressing thug-like was really dressing to impress other men, so that they'd think I was tough, or cool, or intimidating, or scary. None of the kind of women I was into were remotely attracted to that style of dress. And I said to myself, "Do I really care what DUDES think of my clothes? Dudes aren't the ones I'm having problems with right now." So I switched it up.
I've had some friends from the hood who were pretty good with girls, and they always dressed well - button-down shirt; nice, trim jeans (secured firmly at the waist and not hanging down); dress shoes; often a casual blazer or sports jacket. Those guys would pull. I've known a lot of dudes who were ghettofabulous, and I've heard a lot of them claim to be pimping, but I've yet to meet one of them who ever pulled much more than the odd chickenhead here or there.
The kind of girls you'll meet dressed in, say, gym clothes, are totally different than the kinds of girls you'll meet when dressed in a button-down shirt and a tie, even if you're meeting them in the same places (the street, the metro, etc.). Clothes really do make the man... and the guys who dress all thugged-out only end up with hood rats usually who, yeah, are using him more for what they can get from him than anything else a great deal of the time.
Many - not all, but many - women who are raised poor in urban environments by single mothers, as often is the case in the hood (and is in cities around the world, too - you see it everywhere, not just the States), get trained to go after a rich man. Some of the girls do this by improving themselves, and then they're looking for a man of similar quality to their improved selves - education, career, style of dress, etc. The rest though just stay where they are and try to glom onto whoever's ghetto-rich... the pushers, the gangbangers, the guy with a minimum-wage job, and their ilk.
Probably a good call to get away from that if you want a girl who's uplifting herself and encouraging you to be successful too, rather than one who's just scrambling to get whatever she can get from you before you disappear or get shot or get locked up. Those latter girls are bad news, and will push you the opposite direction from having a good life...