Hey Ash, interesting question.
I focus on fashion every once in a while and I ask myself this question on occasions (or the similar question "how to dress well?"). I always learn new things when I do.
At first I thought dressing to impress or dressing well was just "dressing up": expensive clothes and formal clothes like blazers, dressing pants and lots of accessories but..
#1: this is out of place is so many situations. E.g. dressing really formal to day-game at the park can seem off, but be okey in the business district or a charity event.
#2: Dressing up doesn't give you a bad boy image (necessarily). If your personality and how you act is that of a bad boy, dressing up give you depth and attainability for girl that go for business-like men but I think formality and edginess are different parameters… Also depending on your age, and occupation you can get away with more or less of either.
What I try to do is go for a level of formality that is just slightly higher than most men, or that I feel most comfortable with, or just average but well put together, meaning everything fits right, clothes are clean, in good conditions, and colors don't clash.
Then adding items or characteristics that look rebellious/cocky/bad boy.For example: a neat leather jacket, a pair of boots, a t-shirt with deep cuts, ripped jeans, aggressive colors like black or red. Balanced with common items and picked depending of the level of formality. E.g. Chelsea boots over combat boots if the setting is more formal.
Then putting anything that doesn’t fit the rules but reflect your tastes? Snapbacks, khakis, "going out" shirts… (that I don't wear cause I don’t like them but many guys do).
This relating to my last point, dressing well is linked to what you want out of it… Do you prefer something that feels comfortable to you, blend with a specific group that gets you specific kinds of girls, or something versatile..?
I, for example, go for an image that looks very rebellious (cause talking with me at first I don’t give that impression) and eclectic because I naturally don't comfom to stereotypes (ethnicity, hobbies, career-wise), so I try amplify that (with a hard to categorize style) and be a little intriguing…
This is my fashion philosophy. Other guys have given me very valid opinions and that helps evolve these points
Cheers.