@killerman
This is a topic what over at Roosh's the guys used to say is worthless without pics. We have no idea what your badboy style is. I can certainly see myself in some stylish boots which I would consider badboy but these are totally different from what Jesse posted. My badboy style is more like classic 100 year old British brands. I'm just not buying that kind fo footwear right now for many reasons and because of other priorities. But hey, these are still not your grandpa's boots. I mean I totally don't want to be disrespectful of your grandpa. I simply have no idea how much of a style icon he is or isn't.
Style questions usually start by identifying your style-type. Girls Chase' resident style advisor
Darius Belejevas has a test to determine that, but other style advisors use similar style categories for different guys too. I've found another guy called
Tanner Guzy also interesting.
Before you spend any money (quality boots are an investment, like 400 euros) you may be interested in checking out what I wrote as
constructive criticism of Chase' boot design. In that post I linked to The Shoe Snob Blog. Similar resources may start you on a journey of exploring and appreciating gentlemens' footwear. You probably don't have to dig that deep into it than the guy who write that blog to have an edge over 99% of guys however.